2,6-Dimethoxybenzaldehyde → N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-(alpha-hydroxy-2,6-dimethoxybenzyl)thieno[2,3-b]pyridine-3-sulfonamide

HRID 1265035Notes

Reaction equation

HRID 1265035 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]CCCC.[CH3:32][O:33][C:34]1[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH3:43])[C:35]=1[CH:36]=[O:37]>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:36]([OH:37])[C:35]1[C:38]([O:42][CH3:43])=[CH:39][CH:40]=[CH:41][C:34]=1[O:33][CH3:32])(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 964042,6-DimethoxybenzaldehydeHCID 18614049N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxy-methyl)thieno[2,3-b]pyridine-3-sulfonamideHCID 178418339Butyllithium

Product 1

HCID 17894956N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-(alpha-hydroxy-2,6-dimethoxybenzyl)thieno[2,3-b]pyridine-3-sulfonamideYield 63.6%

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-(methoxyethoxymethyl)thieno [2,3-b]pyridine-3-sulfonamide (0.15 g, 0.35 mmoles) [Example 4(A)], THF (5 ml), n-BuLi (2.5 M, 0.16 ml, 0.41 mmoles) and 2,6-dimethoxybenzaldehyde (88 mg, 0.53 mmoles). Flash chromatography (50% EtOAc/hexanes) provided 0.13 g (62%) of the title compound as a pink oil.

Workup

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

Sources & evidence

ORD record
ord-f305120f355149f0892b8e9875603b47
Source dataset
uspto-grants-2003_04
Patent number
US06545014B2

Reaction notes

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