Sodium hydride → HCID 10163495, compound

HRID 1166856Notes

Reaction equation

HRID 1166856 reaction equation
[Br:1][C:2]1[C:3]([CH3:8])=[N:4][O:5][C:6]=1[NH2:7].[H-].[Na+].[CH2:11]([C:13]1[CH:32]=[CH:31][C:16]([CH2:17][C:18]2[S:22][C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[C:19]=2[S:27](Cl)(=[O:29])=[O:28])=[CH:15][CH:14]=1)[CH3:12]>C1COCC1>[Br:1][C:2]1[C:3]([CH3:8])=[N:4][O:5][C:6]=1[NH:7][S:27]([C:19]1[C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[S:22][C:18]=1[CH2:17][C:16]1[CH:15]=[CH:14][C:13]([CH2:11][CH3:12])=[CH:32][CH:31]=1)(=[O:28])=[O:29]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 104875194-Bromo-3-methylisoxazol-5-amineHCID 22998463HCID 22998463, compound

Product 1

HCID 10163495HCID 10163495, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-bromo-3-methyl-5-isoxazolyl)-2-(4-ethylbenzyl) benzo[b]-thiophene-3-sulfonamide was prepared by the method of Example 41 using 4-bromo-3-methyl-5-aminoisoxazole (1.0 mmoles, 0.177 g), NaH (2.5 mmoles, 100 mg), 2-(4-ethylbenzyl)benzo[b]thiophene-3-sulfonyl chloride (1.2 mmoles, 0.42 g) and THF (6 ml). Flash chromatography (50% ethyl acetate/hexanes) followed by recrystallization from chloroform and hexanes provided 0.21 g (43%) of a tan solid, m.p. 128-130° C.

Workup

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

Sources & evidence

ORD record
ord-5820f3570df84a6d977f089cb8362a08
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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