N-(2,6-Difluoro-3-hydroxy-phenyl)-2, 3-dimethyl-5-phenyl-benzamide → 3-[(2,3-Dimethyl-5-phenyl-phenyl)methylamino]-2,4-difluoro-phenol

HRID 1771835Notes

Reaction equation

[F: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]=[CH:20][CH:19]=2)[CH:15]=[C:14]([CH3:24])[C:13]=1[CH3:25]>C1COCC1>[CH3:25][C:13]1[C:14]([CH3:24])=[CH:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:17][C:12]=1[CH2:11][NH:10][C:3]1[C:2]([F:1])=[C:7]([OH:8])[CH:6]=[CH:5][C:4]=1[F:9]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N-(2,6-difluoro-3-hydroxy-phenyl)-2,3-dimethyl-5-phenyl-benzamide (210 mg, 0.6 mmol, 1.0 eq) in THF (4 mL) at 0° C. was added dropwise a solution of BH3 (1M in THF, 3.6 mL, 3.6 mmol, 6.0 eq). The reaction mixture was heated at 60° C. for 5 h, then cooled and quenched by addition of water. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 100:0 to 10:1) to give the title compound as colorless oil (120 mg, 60%).

Workup

temperaturecooled
customquenched by addition of water
extractionThe aqueous layer was extracted with EtOAc
washthe combined organic extracts were washed with water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
customThe residue obtained
customwas purified by column chromatography (petroleum ether:EtOAc, 100:0 to 10:1)

Sources & evidence

ORD record: ord-c0a92c5b7c1440c8acffd8b2980c9304
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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