Reference of 1120-82-7, The chemical industry reduces the impact on the environment during synthesis 1120-82-7, name is (1H-Pyrazol-1-yl)methanol, I believe this compound will play a more active role in future production and life.
To a Schlenk tube was added Cul (9.5 mg), Pd(Ph3P)2Cl2 (35 mg), compound A (1085) (188 mg, 0.5 mmol), TMS acetylene (98 mg, 1.0 mmol), DMF (2 mL), and Et3N (0.5 mL). The reaction mixture was heated at 80 C for 12 hours. The reaction mixture was cooled and treated with EtOAc and brine. The organic layer was separated, dried, and evaporated. The residue was chromatographed on silica gel to give the TMS intermediate. The TMS intermediate was treated with TBAF (0.6 mmol) in 2 mL dry THF for 15 min. The residue was chromatographed on silica gel to give compound C (115 mg, 17% yield). (1086) [0621] To a solution of (lH-pyrazol-l-yl)methanol (196 mg, 2 mmol) in DCM (2 mL) was added methanesulfonyl chloride (4 mmol). The mixture was stirred at 0 C for 10 minutes then Et3N (6 mmol) was slowly added. After stirring at r.t. for 30 min, all volatiles were removed. 3-(4-Hydroxy-l-oxoisoindolin-2-yl)piperidine-2,6-dione (520 mg, 2 mmol), KHC03 (400 mg, 4 mmol), KI (10 mg) and 4 mL CH3CN were added to the residue. The mixture was heated at reflux overnight. The residue was chromatographed on silica gel to give compound D (210 mg, 31% yield). (1087) [0622] To a solution of compound D (210 mg, 0.62 mmol) in acetic acid (4 mL) was added NIS (321 mg, 0.75 mmol). The reaction was stirred for 1 h prior to being concentrated. The residue was purified by HPLC to afford compound E (156 mg, 54%). ESI-MS: 481.05. (1088) [0623] To a Schlenk tube was added Cul (2 mg), Pd(Ph3P)2Cl2 (4 mg), compound C (1089) (20 mg, 0.06 mmol), compound E (28 mg, 0.06 mmol), DMF (2 mL), and Et3N (0.5 mL). The reaction mixture was heated at 80 C for 12 hours. The reaction mixture was cooled and treated with EtOAc and brine. The organic layer was separated, dried, and evaporated. The residue was subjected to HPLC purification to afford Cpd. No. 82 (25 mg, 64% yield). ESI-MS: 674.05.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, (1H-Pyrazol-1-yl)methanol, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; WANG, Shaomeng; HU, Yang; QIN, Chong; XU, Fuming; HU, Jiantao; ZHOU, Bing; CHEN, Zhou; FERNANDEZ-SALAS, Ester; BAI, Longchuan; McEACHERN, Donna; (198 pag.)WO2018/52945; (2018); A1;,
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