N-(2-chloro-6-fluoro-3-hydroxy-phenyl)-2-fluoro-5-(3-fluorophenyl)benzamide → 2-Chloro-4-fluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenol

HRID 1771666Notes

Reaction equation

[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[NH:10][C:11](=O)[C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)[CH:15]=[CH:14][C:13]=1[F:25]>C1COCC1>[Cl:1][C:2]1[C:3]([NH:10][CH2:11][C:12]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)[CH:15]=[CH:14][C:13]=2[F:25])=[C:4]([F:9])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N-(2-chloro-6-fluoro-3-hydroxy-phenyl)-2-fluoro-5-(3-fluorophenyl) benzamide (180 mg, 0.48 mmol, 1.0 eq) in THF (2.5 mL) at 0° C. under N2 was added dropwise a solution of BH3 (1M in THF, 2.86 mL, 2.86 mmol, 6.0 eq). The reaction mixture was heated at 60° C. for 3 h, then cooled and quenched by addition of water. The mixture was extracted with EtOAc and the organic extract was washed with NaHCO3, water and brine, dried (Na2SO4), filtered, evaporated in vacuo and purified by column chromatography (EtOAc:petroleum ether, 1:10, 1.2:10) to give the title compound as an oil (144 mg, 83%).

Workup

temperaturecooled
customquenched by addition of water
extractionThe mixture was extracted with EtOAc
extractionthe organic extract
washwas washed with NaHCO3, water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
custompurified by column chromatography (EtOAc:petroleum ether, 1:10, 1.2:10)

Sources & evidence

ORD record: ord-0fe9b511bc104bc3a459bd2cc89c77d6
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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