Pyridine → 2-Chloro-N-(4-fluoro-2-phenylaminophenyl)acetamide

HRID 243002Notes

Reaction equation

[Cl:1][CH2:2][C:3](Cl)=[O:4].[F:6][C:7]1[CH:8]=[C:9]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]([NH2:13])=[CH:11][CH:12]=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:1][CH2:2][C:3]([NH:13][C:10]1[CH:11]=[CH:12][C:7]([F:6])=[CH:8][C:9]=1[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

Chloroacetyl chloride (0.68 mL, 8.58 mmol) was added dropwise to a stirred solution of 4-fluoro-N2-phenylbenzene-1,2-diamine (1.24 g, 6.13 mmol) and pyridine (2.0 mL, 24.5 mmol) in DCM (8 mL) at 0° C. under a nitrogen atmosphere. Stirring at 0° C. was continued for 20 min then at RT for 2 h. The reaction mixture was partitioned between aq. 1M HCl (50 mL) cooled to 0° C. and DCM. The aqueous phase was further extracted with DCM (×3) and the combined organic fractions were washed with water, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 30-100% DCM in cyclohexane) to afford the title compound as a white crystalline solid (750 mg, 44%). LCMS (Method C): RT 3.39 min [M+H]+ 279.2.

Workup

waitat RT for 2 h
customThe reaction mixture was partitioned between aq. 1M HCl (50 mL)
temperaturecooled to 0° C.
extractionThe aqueous phase was further extracted with DCM (×3)
washthe combined organic fractions were washed with water
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe resulting residue was purified by column chromatography (Si—PCC, gradient 30-100% DCM in cyclohexane)

Sources & evidence

ORD record: ord-d27c4cdf58354c5c84aa1bf344809083
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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