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

HRID 1771642Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N-(6-chloro-2-fluoro-3-hydroxy-phenyl)-2-fluoro-5-(3-fluorophenyl)benzamide (200 mg, 0.53 mmol, 1.0 eq) in THF under N2 was added dropwise a solution of BH3 (1M in THF, 2.65 mL, 2.65 mmol, 5.0 eq) at room temperature. The reaction mixture was heated at 60° C. for 3 h. After cooling, the resulting mixture was quenched by addition of 1M HCl and the mixture extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:4) to give the title compound as an oil (130 mg, 68%).

Workup

temperatureAfter cooling
customthe resulting mixture was quenched by addition of 1M HCl
extractionthe mixture extracted with EtOAc
dry with materialThe combined organic extracts were dried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
customThe residue was purified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:4)

Sources & evidence

ORD record: ord-82044bb561cb4c10bb31d28e6b2417de
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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