Diisopropylethylamine → N-(2-chloro-5-formylphenyl)-5-methylisoxazole-3-carboxamide

HRID 1801571

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH:5]=[O:6].C(N(C(C)C)C(C)C)C.[CH3:20][C:21]1[O:25][N:24]=[C:23]([C:26](Cl)=[O:27])[CH:22]=1>C(Cl)Cl.CCOC(C)=O>[Cl:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[NH:1][C:26]([C:23]1[CH:22]=[C:21]([CH3:20])[O:25][N:24]=1)=[O:27]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-amino-4-chlorobenzaldehyde 2 (0.267 g, 1.72 mmol) in DCM (5 mL) at 0° C. was added N-ethyl-N-isopropylpropan-2-amine (0.600 mL, 3.44 mmol) and 5-methylisoxazole-3-carbonyl chloride (0.292 g, 2.01 mmol). The reaction mixture was stirred at 0° C. for 30 min, warmed to room temperature, stirred for 1 h, and diluted with EtOAc. The organic phase was washed with saturated NaHCO3 (1×), brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 15% to 50% EtOAc in hexanes) gave N-(2-chloro-5-formylphenyl)-5-methylisoxazole-3-carboxamide 3 (0.117 g, 25.8% yield) as a white solid. Mass spectrum: calculated for C12H9ClN2O3 264.0. found 265.0 (M++1).

Workup

temperaturewarmed to room temperature
stirringstirred for 1 h
washThe organic phase was washed with saturated NaHCO3 (1×), brine (1×)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by flash column chromatography on silica gel (eluted with 15% to 50% EtOAc in hexanes)

Sources & evidence

ORD record: ord-97b7ab958b164becbed46e3827144cf0
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349831B2

Linked notes

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