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

HRID 1771748Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-fluoro-N-(6-fluoro-3-hydroxy-2-methyl-phenyl)-5-(3-fluorophenyl)-3-methyl-benzamide (404 mg, 1.1 mmol, 1.0 eq) in THF (10 mL) under N2 was added a solution of BH3 (1M in THF, 5.5 mL, 5.5 mmol, 5.0 eq) at room temperature. The reaction mixture was heated at 60° C. for 3 h, then cooled to room temperature and quenched with 1 M HCl. Water was added and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filtered and evaporated in vacuo. The crude residue obtained was purified by column chromatography (petroleum ether:EtOAc, 100:1 to 15:1) to give the title compound as a yellow oil (269 mg, 69%).

Workup

temperaturecooled to room temperature
customquenched with 1 M HCl
additionWater was added
extractionthe aqueous layer was extracted with EtOAc
dry with materialThe combined organic extracts were dried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
customThe crude residue obtained
customwas purified by column chromatography (petroleum ether:EtOAc, 100:1 to 15:1)

Sources & evidence

ORD record: ord-5362caa385644320b1e237013c3314e6
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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