2-Amino-5-chloro-3-fluoro-N-methoxy-N-methyl-benzamide → (2-Amino-5-chloro-3-fluoro-phenyl)-phenyl-methanone

HRID 1497229Notes

Reaction equation

[NH2:1][C:2]1[C:13]([F:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:3]=1[C:4](N(OC)C)=[O:5].[C:16]1([Mg]Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(OCC)C>[NH2:1][C:2]1[C:13]([F:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:3]=1[C:4]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-amino-5-chloro-3-fluoro-N-methoxy-N-methyl-benzamide (250 mg, 1.07 mmol) in diethyl ether (5 ml) was added phenylmagnesium bromide (2.69 ml, 1M in THF, 2.69 mmol) dropwise at 0° C. The resulting mixture was stirred for 2.5 h at 0° C. and the quenched by addition of saturated NH4Cl solution. The mixture was extracted with EtOAc and the combined organic extracts were washed with brine, dried with Na2SO4 and evaporated. The remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 98:2-95:5) to afford the title compound (189 mg, 70%) as yellow solid. MS (ESI): 250.2 (M+H)+.

Workup

customthe quenched by addition of saturated NH4Cl solution
extractionThe mixture was extracted with EtOAc
washthe combined organic extracts were washed with brine
dry with materialdried with Na2SO4
customevaporated
customThe remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 98:2-95:5)

Sources & evidence

ORD record: ord-b79081a81cd94b548b6c2fd895c68d76
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199938B2

Reaction notes

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