Sodium hydride → HCID 66578576, compound

HRID 1528691Notes

Reaction equation

HRID 1528691 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([CH3:15])[C:11]=2[NH2:16])=[CH:6][CH:5]=1.[CH2:17]([N:24]=[C:25]=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[CH2:17]([NH:24][C:25]([NH:16][C:11]1[C:12]([CH3:15])=[N:13][O:14][C:10]=1[C:7]1[CH:6]=[CH:5][C:4]([Br:3])=[CH:9][CH:8]=1)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76639Benzyl isocyanateHCID 582185375-(4-Bromophenyl)-3-methylisoxazol-4-amine

Product 1

HCID 66578576HCID 66578576, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 0.040 g, 1.00 mmol) was added to a solution of 5-(4-bromo-phenyl)-3-methyl-isoxazol-4-ylamine (0.170 g, 0.67 mmol) in DMF, and the mixture was stirred for 5 minutes at room temperature. Benzyl isocyanate (0.08 mL, 0.67 mmol) was added, and the reaction was stirred at 80° C. for 2 hours. After aqueous workup, the crude material was used directly in the coupling step.

Workup

  1. stirringthe reaction was stirred at 80° C. for 2 hours

Sources & evidence

ORD record
ord-5d589bb95a4a479f8315f6994d152b61
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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