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

HRID 1265028Notes

Reaction equation

HRID 1265028 reaction equation
[Cl:1][C:2]1[C:3]([N:8]([CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])[S:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[S:14][CH:13]=2)(=[O:11])=[O:10])=[N:4][O:5][C:6]=1[CH3:7].[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]([N:8]([CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])[S:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[S:14][C:13]=2[CH:35]([OH:36])[C:34]2[CH:37]=[C:38]3[O:43][CH2:42][O:41][C:39]3=[CH:40][C:33]=2[CH3:32])(=[O:11])=[O:10])=[N:4][O:5][C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 31462426-Methyl-2H-1,3-benzodioxole-5-carbaldehydeHCID 17894957N-(4-chloro-5-methyl-3-isoxazolyl)-N-(methoxyethoxymethyl)thieno[2,3-b]pyridine-3-sulfonamideHCID 178418306HCID 178418306, compound

Product 1

HCID 18614043N-(4-chloro-5-methyl-3-isoxazolyl)-N-(methoxyethoxymethyl)-2-[alpha-hydroxy-2-methyl-4,5-(methylenedioxy)-benzyl]thieno[2,3-b]pyridine-3-sulfonamidYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by the method of Example 4(B) using N-(4-chloro-5-methyl-3-isoxazolyl)-N-(methoxyethoxymethyl)thieno [2,3-b]pyridine-3-sulfonamide (0.23 g, 0.54 mmoles), THF (5 ml), t-BuLi (1.7 M, 0.41 ml, 0.70 mmoles) and 2-methyl-4,5-(methylenedioxy)benzaldehyde (0.13 g, 0.81 mmoles)[Example 6(A)]. Flash chromatography (40% EtOAc/hexanes) provided 0.11 g (36%) of the title compound as a light orange oil.

Workup

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

Sources & evidence

ORD record
ord-eb5c43a9786942a984a9f941e54bf2a0
Source dataset
uspto-grants-2003_04
Patent number
US06545014B2

Reaction notes

Loading…