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

HRID 1771754Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N-(6-fluoro-3-hydroxy-2-methyl-phenyl)-3-(3-fluorophenyl)-5-methyl-benzamide (394 mg, 1.11 mmol, 1.0 eq) in THF (15 mL) under N2 was added a solution of BH3 (1M in THF, 6.7 mL, 6.7 mmol, 6.0 eq) dropwise The reaction mixture was heated at 60° C. overnight. After cooling, the reaction was quenched by addition of water and the aqueous layer was extracted with EtOAc. The extract was washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 30:1 to 20:1) to give the title compound as a brown oil (324 mg, 86%).

Workup

temperatureAfter cooling
customthe reaction was quenched by addition of water
extractionthe aqueous layer was extracted with EtOAc
washThe extract was washed with water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
customThe residue obtained
customwas purified by column chromatography (petroleum ether:EtOAc, 30:1 to 20:1)

Sources & evidence

ORD record: ord-563452352ae8425c9184233cffcbcf91
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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