HCID 59463785, compound → HCID 59463787, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 200 mg (0.4 mmol) of 3-methyl-5-nitro-4-[5,5,5-trifluoro-4-hydroxy-4-(6-methanesulfonyl-4-methylchroman-4-ylmethyl)pent-1-ynyl]benzonitrile and 375 mg (6.7 mmol) of iron powder in 4 mL of ethanol and 2 mL of acetic acid was warmed at 90° C. After 2 hours, the mixture was cooled and diluted with 50 mL of ethyl acetate and filtered through CELITE® filter aid. The filtrate was washed with three portions of saturated aqueous sodium bicarbonate, dried over sodium sulfate, and concentrated in vacuo to afford 130 mg (68%) of 3-amino-5-methyl-4-[5,5,5-trifluoro-4-hydroxy-4-(6-methanesulfonyl-4-methylchroman-4-ylmethyl)pent-1-ynyl]benzonitrile as a brown oil.

Provenance & Evidence