HCID 89444094, compound → 2,4-Difluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-5-methyl-phenol

HRID 1771738Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

N-(2,6-difluoro-3-hydroxy-5-methyl-phenyl)-2-fluoro-5-(3-fluorophenyl)benzamide (285 mg, 0.76 mmol, 1.0 eq) was dissolved in THF (20 mL). A solution of BH3 (1M in THF, 4.56 mL, 4.56 mmol, 6.0 eq) was added and the reaction mixture heated at 60° C. under nitrogen for 2 h. After cooling, the reaction was quenched with water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography (petroleum ether: EtOAc, 30:1 to 20:1) to give the title compound as a colorless oil (206 mg, 75%).

Workup

temperatureAfter cooling
customthe reaction was quenched with water
extractionextracted with EtOAc
washThe combined organic extracts were washed with water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
customThe residue was purified by column chromatography (petroleum ether: EtOAc, 30:1 to 20:1)

Sources & evidence

ORD record: ord-b66b31eb8a6c481da7477f6da5579337
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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