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

HRID 1771655Notes

Reaction equation

[F:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]([OH:14])[C:8]=1[CH3:15])=O>C1COCC1>[F:13][C:12]1[CH:11]=[CH:10][C:9]([OH:14])=[C:8]([CH3:15])[C:7]=1[NH:6][CH2:4][C:3]1[CH:16]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)[CH:18]=[CH:19][C:2]=1[F:1]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-fluoro-N-(6-fluoro-3-hydroxy-2-methyl-phenyl)-5-(3-fluorophenyl)benzamide (300 mg, 0.84 mmol, 1.0 eq) in THF (10 mL) under N2 was added dropwise a solution of BH3 (1M in THF, 4.2 mL, 4.2 mmol, 5.0 eq). The reaction mixture was heated at 50° C. overnight, then cooled and the reaction quenched by addition of 1M HCl. The mixture was extracted with EtOAc and the organic extract was washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title product as an oil (200 mg, 69%).

Workup

temperaturecooled
customthe reaction quenched by addition of 1M HCl
extractionThe mixture was extracted with EtOAc
extractionthe organic extract
washwas washed with water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-e8da800a44a94da6b1247cd82b288498
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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