Water → HCID 117601838, compound

HRID 1773758Notes

Reaction equation

Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH3:12][C:13]1[C:17](B2OC(C)(C)C(C)(C)O2)=[C:16]([CH3:27])[O:15][N:14]=1.O>CCOC(C)=O>[CH3:12][C:13]1[C:17]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=2)=[C:16]([CH3:27])[O:15][N:14]=1

Participants

Conditions

Temperature: 120 °C

Procedure

4-bromo-2-nitroaniline (1 g, 4.6 mmol) and 3,5-Dimethylisoxazole-4-boronic acid pinacol ester (2 g, 9.2 mmol) was added to a solvent mixture of 1,2-dimethoxymethane (12 ml) and water (6 ml). To the above mixture were added PEPPSI-Ipr (312 mg, 0.46 mmol) and CsCO3 (4.5 g, 13.8 mmol). The reaction mixture was heated at 120° C. for 30 min. The reaction mixture was then diluted with EtOAc (100 ml), washed with bring (50 ml×2). The organic solvent was evaporated and the residue was dissolved in DCM and purified with flash column chromatography (50% EtOAc/Hexane) to afford 4-(3,5-dimethylisoxazol-4-yl)-2-nitroaniline.

Workup

washwashed
customThe organic solvent was evaporated
dissolutionthe residue was dissolved in DCM
custompurified with flash column chromatography (50% EtOAc/Hexane)

Sources & evidence

ORD record: ord-88b55aa2158e4f2fa069d8c097e228e4
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255089B2

Reaction notes

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