6-(5-Fluoro-2-methylphenyl)-1-(3-fluoro-2-nitrophenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol → 1-(2-Amino-3-fluorophenyl)-6-(5-fluoro-2-methylphenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol

HRID 400669Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A stirred solution of 6-(5-fluoro-2-methylphenyl)-1-(3-fluoro-2-nitrophenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol (1.05 g, 2.4 mmol) in 6 mL of absolute ethanol and 2 mL of glacial acetic acid was treated with iron powder (800 mg, 14.3 mmol). The resulting mixture was heated at 80° C. for 2 hours, cooled to room temperature, diluted with diethyl ether, filtered through a pad of CELITE® filter aid, and concentrated in vacuo. The residue was dissolved in diethyl ether, treated with anhydrous potassium carbonate, filtered, and concentrated in vacuo to give 900 mg of 1-(2-amino-3-fluorophenyl)-6-(5-fluoro-2-methylphenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol as a light brownish oil (92% yield), which was used without purification.

Workup

temperaturecooled to room temperature
filtrationfiltered through a pad of CELITE®
filtrationfilter aid
concentrationconcentrated in vacuo
dissolutionThe residue was dissolved in diethyl ether
additiontreated with anhydrous potassium carbonate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6d52490ef06e43969390be80ce4b6ca9
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741897B2

Reaction notes

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