Category: 27258-33-9

A common heterocyclic compound, 27258-33-9, name is 1-Methyl-1H-pyrazole-5-carbaldehyde, molecular formula is C5H6N2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 27258-33-9.

To a mixture of compound OI-5a (2 g, 18.2 mmol, 1.0 eq) in DMF (20 mL) was added NBS (4.86 g, 27.3 mmol, 1.5 eq). The mixture was stirred at room temperature for 16 h under nitrogen atmosphere. Then the mixture was filtered and extracted with water and ethyl acetate. The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford compound OI-5b (2.3 g, 67%).

The synthetic route of 1-Methyl-1H-pyrazole-5-carbaldehyde has been constantly updated, and we look forward to future research findings.

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 27258-33-9, name is 1-Methyl-1H-pyrazole-5-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. 27258-33-9

Example 203 Rac-(4bR,5R,6R,7S,7aR)-7a-(4-bromophenyl)-6-(hydroxymethyl)-4-methoxy-5-((((1-methyl-1H-pyrazol-5-yl)methyl)amino)methyl)-7-phenyl-5,6,7,7a-tetrahydro-4bH-cyclopenta[4,5]furo[2,3-c]pyridin-4b-ol (Cpd. No. 203F) (1387) Synthesis of rac-(4bR,5R,6R,7S,7aR)-7a-(4-bromophenyl)-6-(hydroxymethyl)-4-methoxy-5-((((1-methyl-1H-pyrazol-5-yl)methyl)amino)methyl)-7-phenyl-5,6,7,7a-tetrahydro-4bH-cyclopenta[4,5]furo[2,3-c]pyridin-4b-ol (Cpd. No. 203F) (1388) To a solution of 1631 rac-(4bR,5R,6R,7S,7aR)-5-(aminomethyl)-7a-(4-bromophenyl)-6-(hydroxymethyl)-4-methoxy-7-phenyl-5,6,7,7a-tetrahydro-4bH-cyclopenta[4,5]furo[2,3-c]pyridin-4b-ol (1, 50 mg, 0.10 mmol) in 11 THF (1 mL) were added 1799 2-methylpyrazole-3-carbaldehyde (12 muL, 13 mg, 0.12 mmol), 17 acetic acid (1.2 muL, 1.3 mg, 0.021 mmol) and molecular sieves (ca. 80 mg). The mixture was stirred for 30 min. Then 41 sodium triacetoxyborohydride (85 mg, 0.40 mmol) was added, and the mixture was stirred for 30 min. Another 3 muL (3 mg, 0.03 mmol) 2-methylpyrazole-3-carbaldehyde were added. After another 30 min the reaction was quenched with 1682 NaHCO3(aq), and the mixture was extracted (3¡Á dichloromethane). The combined organic phases were dried (Na2SO4), filtered and concentrated. The crude product was taken up in MeCN/DMSO/water. And subjected to HPLC purification (C18, MeCN/H2O+0.1% TFA) to provide product 1800 rac-(4bR,5R,6R,7S,7aR)-7a-(4-bromophenyl)-6-(hydroxymethyl)-4-methoxy-5-((((1-methyl-1H-pyrazol-5-yl)methyl)amino)methyl)-7-phenyl-5,6,7,7a-tetrahydro-4bH-cyclopenta[4,5]furo[2,3-c]pyridin-4b-ol (Cpd. No. 203F) as its TFA salt. Yield: 40.5 mg (0.0574 mmol, 57%), white solid; MS (ESI) m/z 591.3 [M+1]+; 1H NMR (400 MHz, DMSO-d6) delta 9.14 (b, 1H), 8.52 (b, 1H), 8.21 (s, 1H), 8.13 (s, 1H), 7.52 (d, J=1.9 Hz, 1H), 7.34 (d, J=8.6 Hz, 2H), 7.14-7.08 (m, 5H), 6.85-6.80 (m, 2H), 6.53 (d, J=1.9 Hz, 1H), 6.35 (s, 1H), 5.52 (b, 1H), 4.63-4.48 (m, 2H), 3.92 (s, 3H), 3.91 (s, 3H), 3.78-3.68 (m, 1H), 3.54-3.44 (m, 1H), 3.45 (dd, J=11.1, 2.5 Hz, 1H), 3.27 (d, J=13.6 Hz, 1H), 3.21 (dd, J=11.4, 6.8 Hz, 1H), 3.10-3.02 (m, 1H), 2.76-2.66 (m, 1H).

The synthetic route of 27258-33-9 has been constantly updated, and we look forward to future research findings.

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 27258-33-9, name is 1-Methyl-1H-pyrazole-5-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. 27258-33-9

Example 203 Rac-(4bR,5R,6R,7S,7aR)-7a-(4-bromophenyl)-6-(hydroxymethyl)-4-methoxy-5-((((1-methyl-1H-pyrazol-5-yl)methyl)amino)methyl)-7-phenyl-5,6,7,7a-tetrahydro-4bH-cyclopenta[4,5]furo[2,3-c]pyridin-4b-ol (Cpd. No. 203F) (1387) Synthesis of rac-(4bR,5R,6R,7S,7aR)-7a-(4-bromophenyl)-6-(hydroxymethyl)-4-methoxy-5-((((1-methyl-1H-pyrazol-5-yl)methyl)amino)methyl)-7-phenyl-5,6,7,7a-tetrahydro-4bH-cyclopenta[4,5]furo[2,3-c]pyridin-4b-ol (Cpd. No. 203F) (1388) To a solution of 1631 rac-(4bR,5R,6R,7S,7aR)-5-(aminomethyl)-7a-(4-bromophenyl)-6-(hydroxymethyl)-4-methoxy-7-phenyl-5,6,7,7a-tetrahydro-4bH-cyclopenta[4,5]furo[2,3-c]pyridin-4b-ol (1, 50 mg, 0.10 mmol) in 11 THF (1 mL) were added 1799 2-methylpyrazole-3-carbaldehyde (12 muL, 13 mg, 0.12 mmol), 17 acetic acid (1.2 muL, 1.3 mg, 0.021 mmol) and molecular sieves (ca. 80 mg). The mixture was stirred for 30 min. Then 41 sodium triacetoxyborohydride (85 mg, 0.40 mmol) was added, and the mixture was stirred for 30 min. Another 3 muL (3 mg, 0.03 mmol) 2-methylpyrazole-3-carbaldehyde were added. After another 30 min the reaction was quenched with 1682 NaHCO3(aq), and the mixture was extracted (3¡Á dichloromethane). The combined organic phases were dried (Na2SO4), filtered and concentrated. The crude product was taken up in MeCN/DMSO/water. And subjected to HPLC purification (C18, MeCN/H2O+0.1% TFA) to provide product 1800 rac-(4bR,5R,6R,7S,7aR)-7a-(4-bromophenyl)-6-(hydroxymethyl)-4-methoxy-5-((((1-methyl-1H-pyrazol-5-yl)methyl)amino)methyl)-7-phenyl-5,6,7,7a-tetrahydro-4bH-cyclopenta[4,5]furo[2,3-c]pyridin-4b-ol (Cpd. No. 203F) as its TFA salt. Yield: 40.5 mg (0.0574 mmol, 57%), white solid; MS (ESI) m/z 591.3 [M+1]+; 1H NMR (400 MHz, DMSO-d6) delta 9.14 (b, 1H), 8.52 (b, 1H), 8.21 (s, 1H), 8.13 (s, 1H), 7.52 (d, J=1.9 Hz, 1H), 7.34 (d, J=8.6 Hz, 2H), 7.14-7.08 (m, 5H), 6.85-6.80 (m, 2H), 6.53 (d, J=1.9 Hz, 1H), 6.35 (s, 1H), 5.52 (b, 1H), 4.63-4.48 (m, 2H), 3.92 (s, 3H), 3.91 (s, 3H), 3.78-3.68 (m, 1H), 3.54-3.44 (m, 1H), 3.45 (dd, J=11.1, 2.5 Hz, 1H), 3.27 (d, J=13.6 Hz, 1H), 3.21 (dd, J=11.4, 6.8 Hz, 1H), 3.10-3.02 (m, 1H), 2.76-2.66 (m, 1H).

The synthetic route of 27258-33-9 has been constantly updated, and we look forward to future research findings.

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 27258-33-9 as follows. 27258-33-9

Example 4; Influence of the ligand Using the optimal conditions [Example 2] which leads to 85-87% ee with the ligand sd499, a ligand screening with a variety of N,O-ligands was carried out. The results are given in the following table. The best results were obtained with the ligands sd311b (91% ee) and commercially available (S)-2-piperidinyl-1,1,2-triphenylethanol at 5 mol% scale. As the latter one is known to be a somewhat slower ligand than the paracyclophane-based ligands and the derivatives of sd499, we repeated the experiment with 10 mol% of (S)-2-piperidinyl-1,1,2-triphenylethanol. This experiment gave 93% ee. The ligand is available in both enantiomeric forms.

According to the analysis of related databases, 27258-33-9, the application of this compound in the production field has become more and more popular.