Sodium hydride → HCID 10117410, compound

HRID 234399Notes

Reaction equation

HRID 234399 reaction equation
[NH2:1][C:2]1[O:6][N:5]=[C:4]([CH3:7])[C:3]=1[Br:8].[H-].[Na+].[CH3:11][O:12][C:13]1[CH:32]=[CH:31][CH:30]=[CH:29][C:14]=1[CH2:15][C:16]1[S:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[C:17]=1[S:25](Cl)(=[O:27])=[O:26]>C1COCC1>[Br:8][C:3]1[C:4]([CH3:7])=[N:5][O:6][C:2]=1[NH:1][S:25]([C:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[S:20][C:16]=1[CH2:15][C:14]1[CH:29]=[CH:30][CH:31]=[CH:32][C:13]=1[O:12][CH3:11])(=[O:26])=[O:27]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 104875194-Bromo-3-methylisoxazol-5-amineHCID 22998419HCID 22998419, compound

Product 1

HCID 10117410HCID 10117410, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-bromo-3-methyl-5-isoxazolyl)-2-(2-methoxybenzyl)benzo[b]thiophene-3-sulfonamide was prepared by the method of Example 41 with 5-amino-4-bromo-3-methylisoxazole (1.0 mmoles, 0.18 g), NaH (2.5 mmoles, 100 mg), 2-(2-methoxybenzyl)-benzo[b]thiophene-3-sulfonyl chloride (1.4 mmoles, 0.49 g) and THF (7ml). Flash chromatography (50% ethyl acetate/hexanes) followed by recrystallization from chloroform and hexanes provided 0.30 g (61%) of a brown solid, m.p. 80°-84° C.

Workup

  1. customFlash chromatography (50% ethyl acetate/hexanes) followed by recrystallization from chloroform and hexanes

Sources & evidence

ORD record
ord-782b82c91909415fb8a2fc3ee00b5f49
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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