Sodium hydride → N-(4-bromo-3-methyl-5-isoxazolyl)-1-methylindole-2-sulfonamide

HRID 234351Notes

Reaction equation

HRID 234351 reaction equation
[Br:1][C:2]1[C:3]([CH3:8])=[N:4][O:5][C:6]=1[NH2:7].[H-].[Na+].[CH3:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[C:13]1[S:21](Cl)(=[O:23])=[O:22]>C1COCC1>[Br:1][C:2]1[C:3]([CH3:8])=[N:4][O:5][C:6]=1[NH:7][S:21]([C:13]1[N:12]([CH3:11])[C:20]2[C:15]([CH:14]=1)=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:22])=[O:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 104875194-Bromo-3-methylisoxazol-5-amineHCID 229985021-Methylindole-2-sulfonyl chloride

Product 1

HCID 23445329N-(4-bromo-3-methyl-5-isoxazolyl)-1-methylindole-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-bromo-3-methyl-5-isoxazolyl)-1-methylindole-2-sulfonamide was prepared by the method of Example 41 with 4-bromo-3-methyl-5-aminoisoxazole (1.0 mmols, 0.18 g), NaH (2.5 mmols, 60 mg), 1-methylindole-2-sulfonyl chloride (1.2 mmols, 0.26 g) and THF (7 ml). Recrystallization from chloroform and hexane provided 0.28 g (77%) of a brown solid, m.p. 132°-134° C.

Workup

  1. customRecrystallization from chloroform and hexane

Sources & evidence

ORD record
ord-ca968f14fb9a47fcb826466ae67b63c9
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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