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

HRID 1771785Notes

Reaction equation

[F:1][C:2]1[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[CH:18][C:17]([CH3:27])=[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]([CH3:27])[CH:18]=[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)[C:2]=1[F:1]

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of 2-fluoro-N-(6-fluoro-3-hydroxy-2-methyl-phenyl)-3-(3-fluorophenyl)-5-methyl-benzamide (200 mg, 0.54 mmol, 1.0 eq) in THF (5 mL) under nitrogen was added a solution of BH3 (1M in THF, 3.0 mL, 3.0 mmol, 5.6 eq) dropwise over 5 min. the mixture was heated at 60° C. overnight, then the reaction cooled to room temperature and quenched by addition of aqueous NH4Cl. The reaction was further diluted with water and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 100:1 to 25:1) to give the title compound as a colorless oil (180 mg, 93%).

Workup

temperaturethe reaction cooled to room temperature
customquenched by addition of aqueous NH4Cl
additionThe reaction was further diluted with water
extractionthe aqueous layer was extracted with EtOAc
dry with materialThe combined organic extracts were dried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
customThe residue obtained
customwas purified by column chromatography (petroleum ether:EtOAc, 100:1 to 25:1)

Sources & evidence

ORD record: ord-174b132f14b3486f94830586f1da8d58
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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