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

HRID 1771824Notes

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]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=2)[CH:15]=[C:14]([CH3:26])[C:13]=1[CH3:27]>C1COCC1>[F:24][C:22]1[CH:23]=[C:18]([C:16]2[CH:15]=[C:14]([CH3:26])[C:13]([CH3:27])=[C:12]([CH2:11][NH:10][C:3]3[C:2]([F:1])=[C:7]([OH:8])[CH:6]=[CH:5][C:4]=3[F:9])[CH:17]=2)[CH:19]=[C:20]([F:25])[CH:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N-(2,6-difluoro-3-hydroxy-phenyl)-5-(3,5-difluorophenyl)-2,3-dimethyl-benzamide (46 mg, 0.12 mmol, 1.0 eq) in THF (5 mL) under N2 was added dropwise a solution of BH3 (1M in THF, 0.72 mL, 0.72 mmol, 6.0 eq). The reaction mixture was heated at 60° C. overnight. After cooling, the resulting mixture was quenched with water and extracted with EtOAc. The organic extract was washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography (petroleum ether:EtOAc, 40:1 to 20:1) to give the title compound as a colorless oil (20 mg, 45%).

Workup

temperatureAfter cooling
customthe resulting mixture was quenched with water
extractionextracted with EtOAc
extractionThe organic extract
washwas washed with water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
customThe residue was purified by column chromatography (petroleum ether:EtOAc, 40:1 to 20:1)

Sources & evidence

ORD record: ord-77a728f1415245458184138c2675da84
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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