1,1,3,3-Tetramethylguanidine → HCID 44544423, compound

Participants

Reaction Conditions

Reaction Steps

N-{2-[(S)-6-(3-Bromophenyl)-4-hydroxy-6-methyl-4-trifluoromethylhept-1-ynyl]-6-methanesulfonylpyridin-3-yl}-2,2,2-trifluoroacetamide (351 mg, 0.57 mmol) was dissolved in 3.4 mL of DMSO and tetramethylguanidine (0.43 mL, 3.42 mmol) was added. The mixture was stirred at 70° C. for 7 hours. Then it was diluted with ethyl acetate, washed with saturated aqueous ammonium chloride solution, and brine, dried over sodium sulfate, and concentrated in vacuo. The mixture was purified by flash chromatography (gradient 0→8% MeOH in DCM). The product was further purified by crystallization (DCM) to give (R)-4-(3-bromophenyl)-1,1,1-trifluoro-2-(5-methanesulfonyl-1H-pyrrolo[3,2-b]pyridin-2-ylmethyl)-4-methylpentan-2-ol as a white solid (181 mg, 61%).

Provenance & Evidence