N-(2,6-dichloro-3-methoxy-phenyl)-2-fluoro-5-(3-fluorophenyl) benzamide → 2,6-Dichloro-N-[[2-fluoro-5-(3-fluorophenyl)phenyl]methyl]-3-methoxy-aniline

HRID 1771681Notes

Reaction equation

[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([Cl: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>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([Cl:10])[C:3]=1[NH:11][CH2:12][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]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N-(2,6-dichloro-3-methoxy-phenyl)-2-fluoro-5-(3-fluorophenyl)benzamide (200 mg, 0.5 mmol, 1.0 eq) in dry THF (10 mL) was added a solution of BH3 (1M in THF, 2 mL, 2 mmol, 4.0 eq) dropwise. The solution was then heated at 60° C. overnight. The reaction was quenched by addition of MeOH, then concentrated and the residue obtained was purified by column chromatography (Petroleum ether:EtOAc, 10:1) to give the title compound (150 mg, 77%).

Workup

customThe reaction was quenched by addition of MeOH
concentrationconcentrated
customthe residue obtained
customwas purified by column chromatography (Petroleum ether:EtOAc, 10:1)

Sources & evidence

ORD record: ord-3b5ee38347de4fc481ee913f9f2cc8f1
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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