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

HRID 1771624Notes

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

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of N-(2,6-difluoro-3-hydroxy-phenyl)-2-fluoro-5-(3-fluorophenyl)-3-methyl-benzamide (200 mg, 0.53 mmol, 1.0 eq) in THF (8 mL) was added a solution of BH3 (1M in THF, 5 mL, 5 mmol, 9.4 eq) dropwise. The reaction was heated at 55° C. for 2 h, then quenched by the addition of 1M HCl and EtOAc. The organic extract was separated, washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound (150 mg, 77%). This material was used without further purification.

Workup

customquenched by the addition of 1M HCl and EtOAc
extractionThe organic extract
customwas separated
washwashed with water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-fe6e7bfede464555aa53e1c5183bd81c
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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