Diisopropylethylamine → N-(2-(tert-butylamino)pyridin-3-yl)-2,3-difluorobenzamide

HRID 1518521Notes

Reaction equation

[C:1]([NH:5][C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[F:22][C:23]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>C(Cl)Cl>[C:1]([NH:5][C:6]1[C:11]([NH:12][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][CH:30]=[C:31]([F:32])[C:23]=2[F:22])=[CH:10][CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N2-tert-butylpyridine-2,3-diamine in dry DCM (150 mL) was added DIEA (17 mL, 95.5 mmol). The solution was cooled to 0° C. and carefully added 2,3-difluorobenzoyl chloride (8.35 g, 47.30 mmol). The reaction was allowed to warm up to RT and stirred for 1 hr. The mixture was then washed with water, saturated NaHCO3, and dried over MgSO4. Removal of the solvent by evaporation, the residue was purified by silica gel chromatography (5%-60% EtOAc/hexane) to yield N-(2-(tert-butylamino)pyridin-3-yl)-2,3-difluorobenzamide (4.0 g, 13.10 mmol); LC-MS m/e=306.1 (M+H).

Workup

temperatureto warm up to RT
washThe mixture was then washed with water, saturated NaHCO3
dry with materialdried over MgSO4
customRemoval of the solvent
customby evaporation
customthe residue was purified by silica gel chromatography (5%-60% EtOAc/hexane)

Sources & evidence

ORD record: ord-5ad8fb4e69904b369b403b453e0b3c70
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232406B2

Reaction notes

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