N-(2,6-Difluoro-3-hydroxy-phenyl)-5-(3,4-difluorophenyl)-2,3-dimethyl-benzamide → HCID 89444144, compound

HRID 1771819Notes

Reaction equation

[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[NH:10][C:11](=O)[C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=2)[CH:15]=[C:14]([CH3:26])[C:13]=1[CH3:27]>C1COCC1>[F:25][C:20]1[CH:19]=[C:18]([C:16]2[CH:15]=[C:14]([CH3:26])[C:13]([CH3:27])=[C:12]([CH2:11][NH:10][C:3]3[C:2]([F:1])=[C:7]([OH:8])[CH:6]=[CH:5][C:4]=3[F:9])[CH:17]=2)[CH:23]=[CH:22][C:21]=1[F:24]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N-(2,6-difluoro-3-hydroxy-phenyl)-5-(3,4-difluorophenyl)-2,3-dimethyl-benzamide (90 mg, 0.23 mmol, 1.0 eq) in THF (1.5 mL) under N2 was added dropwise a solution of BH3 (1M in THF, 1.03 mL, 1.03 mmol, 4.6 eq) at 0° C. The reaction mixture was heated at 60° C. overnight then cooled and the reaction quenched with water. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 30:1 to 15:1) to give the title compound as a colorless oil (70 mg, 81%).

Workup

temperaturethen cooled
customthe reaction quenched with water
extractionThe aqueous layer was extracted with EtOAc
washthe combined organic extracts were washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
customThe residue obtained
customwas purified by column chromatography (petroleum ether:EtOAc, 30:1 to 15:1)

Sources & evidence

ORD record: ord-d6611cdbac9e45e19aa063515cb9a968
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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