HCID 68639170, compound → HCID 68639193, compound

HRID 1713340Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 580 mg (1.2 mmol) of 3-methyl-5-nitro-4-[5,5,5-trifluoro-4-(6-fluoro-4-methylchroman-4-ylmethyl)-4-hydroxypent-1-ynyl]benzonitrile and 1.4 g (24 mmol) of iron powder in 15 mL of ethanol and 10 mL of acetic acid was warmed to 80° C. After 30 minutes, 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, then washed with brine, dried over magnesium sulfate, and concentrated in vacuo to afford 500 mg (92%) of 3-amino-5-methyl-4-[5,5,5-trifluoro-4-(6-fluoro-4-methylchroman-4-ylmethyl)-4-hydroxypent-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
washwashed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-91bdd7a4029449bca0a1c9c71dcbde04
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795272B2

Reaction notes

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