HCID 59463785, compound → HCID 59463787, compound

HRID 1713351Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:35]([O-])=O)[C:9]=1[C:10]#[C:11][CH2:12][C:13]([OH:34])([CH2:18][C:19]1([CH3:33])[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:27]=2)[O:22][CH2:21][CH2:20]1)[C:14]([F:17])([F:16])[F:15])[C:5]#[N:6]>C(O)C.C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:35][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([CH3:1])[C:9]=1[C:10]#[C:11][CH2:12][C:13]([OH:34])([CH2:18][C:19]1([CH3:33])[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:27]=2)[O:22][CH2:21][CH2:20]1)[C:14]([F:17])([F:15])[F:16])[C:5]#[N:6]

Participants

Conditions

Temperature: 90 °C

Procedure

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.

Workup

temperaturethe mixture was cooled
filtrationfiltered through CELITE®
filtrationfilter aid
washThe filtrate was washed with three portions of saturated aqueous sodium bicarbonate
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8b431b1e835b4076a3e63937e605422d
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795272B2

Reaction notes

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