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

HRID 1771628Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-fluoro-N-(2-fluoro-3-hydroxy-6-methyl-phenyl)-5-(3-fluorophenyl)benzamide (500 mg, 1.4 mmol, 1 eq) in THF (10 mL) under N2 was added dropwise a solution of BH3 (1M in THF, 7 mL, 7.0 mmol, 5 eq). The reaction mixture was heated at 50° C. overnight. After cooling, the resulting mixture was quenched by addition of 1M HCl and extracted with EtOAc. The organic extract was washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as an oil (300 mg, 42%).

Workup

temperatureAfter cooling
customthe resulting mixture was quenched by addition of 1M HCl
extractionextracted with EtOAc
extractionThe organic extract
washwas washed with water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-81aeb960798b430598b57b6ddfed9647
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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