6-Methyl-2H-1,3-benzodioxole-5-carbaldehyde → N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[alpha-hydroxy-2-methyl-4,5-(methylenedioxy)-benzyl]thieno [2,3-b]pyridine-3-sulfonamide

HRID 2268993Notes

Reaction equation

HRID 2268993 reaction equation
[Cl:1][C:2]1[C:3]([CH3:26])=[N:4][O:5][C:6]=1[N:7]([CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])[S:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[S:13][CH:12]=1)(=[O:10])=[O:9].[Li]C(C)(C)C.[CH3:32][C:33]1[CH:40]=[C:39]2[O:41][CH2:42][O:43][C:38]2=[CH:37][C:34]=1[CH:35]=[O:36]>C1COCC1>[Cl:1][C:2]1[C:3]([CH3:26])=[N:4][O:5][C:6]=1[N:7]([CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])[S:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[S:13][C:12]=1[CH:35]([OH:36])[C:34]1[CH:37]=[C:38]2[O:43][CH2:42][O:41][C:39]2=[CH:40][C:33]=1[CH3:32])(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 31462426-Methyl-2H-1,3-benzodioxole-5-carbaldehydeHCID 18614049N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxy-methyl)thieno[2,3-b]pyridine-3-sulfonamideHCID 178418306HCID 178418306, compound

Product 1

HCID 18614054N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[alpha-hydroxy-2-methyl-4,5-(methylenedioxy)-benzyl]thieno [2,3-b]pyridine-3-sulfonamideYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by the method of Example 4(B) using N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxy-methyl)thieno[2,3-b]pyridine-3-sulfonamide (0.31 g, 0.75 mmoles)[Example 4(A)], THF (4 ml), t-BuLi (1.7 M, 0.53 ml, 0.90 mmoles) and 2-methyl-4,5-(methylenedioxy)benzaldehyde (0.15 g, 0.90 mmoles). Flash chromatography (40% EtOAc/hexanes) provided 0.16 g (38%) of the title compound.

Workup

  1. customThe title compound was prepared by the method of Example 4(B)

Sources & evidence

ORD record
ord-dc5a3ef4446b4e7582b995d847114c25
Source dataset
uspto-grants-2001_12
Patent number
US06329387B2

Reaction notes

Loading…