Related Products of 1227611-94-0,Some common heterocyclic compound, 1227611-94-0, name is 4-(4-Iodo-1H-pyrazol-1-yl)cyclohexanone, molecular formula is C9H11IN2O, 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.
Example 89: 4-(4-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5- yl}-pyrazol-1-yl)cyclohexanone[428] A 20 ml sealable vial was charged with 3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-5- (4,4,5,5-tetramethyl[1 ,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (80.0 mg, 0.156 mmol), 4-(4-lodopyrazol-1-yl)cyclohexanone (52.5 mg, 0.172 mmol), Pd(PPh3)4 (12.0 mg, 0.0103 mmol), potassium carbonate (71.8 mg, 0.514 mmol), and 4:1 dioxane:water (5 mL). The cap was sealed and the vial was evacuated and backfilled with nitrogen (3x). After that, the vial was heated at 90 C for 2 h. The reaction mixture was partitioned between EtOAc/H2O (15 ml/10 ml). The aqueous phase was extracted with EtOAc (10 ml). The combined organic extracts were washed with water (10 ml) and brine (10 ml), dried over MgSO4, filtered, and concentrated in vacuo to give a brown oil that was purified by prep. TLC eluting with 4% MeOH/DCM to give the title compound. 1H NMR (400 MHz, CDCI3 ): delta = 1.88 (d, J = 7.2 Hz, 3 H), 2.31-2.68 (m, 8 H), 4.64 (tt, J = 1 1.8, 4.0 Hz, 1 H), 5.28 (q, J = 7.2 Hz, 1 H), 7.01 (dd, J = 8.0 & 8.8 Hz, 1 H), 7.30 (s, 1 H), 7.32 (brs, 1 H), 7.48 (s, 1 H), 7.60 (d, J = 0.8 Hz, 1 H), 7.66 (d, J = 0.8 Hz, 1 H), 8.41 (brs, 1 H), 9.77 (brs, 1 H). MS(ES+): m/z = 471.16/473.11 (100/68) [MH+]. HPLC: tR = 3.39 min (polar_5 min, ZQ3).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-Iodo-1H-pyrazol-1-yl)cyclohexanone, its application will become more common.
Reference:
Patent; OSI PHARMACEUTICALS, INC.; CHEN, Xin; JIN, Meizhong; KLEINBERG, Andrew; LI, An-hu; MULVIHILL, Mark, J.; STEINIG, Arno, G.; WANG, Jing; WO2010/59771; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics