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

HRID 1771766Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of N-(6-fluoro-3-hydroxy-2-methyl-phenyl)-3-(3-fluorophenyl)-5-methoxy-benzamide (500 mg, 1.35 mmol, 1.0 eq) in anhydrous THF (10 mL) under N2 was added a solution of BH3 (1M in THF, 7 mL, 6.77 mmol, 5.0 eq) dropwise over 5 min. The reaction mixture was heated to 60° C. overnight. After cooling, the resulting mixture was quenched by addition of saturated aqueous NH4Cl. Water was added and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filtered and evaporated in vacuo. The crude product was purified by column chromatography (petroleum ether:EtOAc, 100:1 to 20:1) to give the title compound as a colorless oil (390 mg, 81%).

Workup

temperatureAfter cooling
customthe resulting mixture was quenched by addition of saturated aqueous NH4Cl
additionWater was added
extractionthe aqueous layer was extracted with EtOAc
dry with materialThe combined organic extracts were dried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
customThe crude product was purified by column chromatography (petroleum ether:EtOAc, 100:1 to 20:1)

Sources & evidence

ORD record: ord-e2ca468a72c64c3cb6e5f5748f9dcad5
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

Loading…