Sodium hydride → Ethyl 4-(3,4-dichlorobenzyl)thieno[3,2-b]pyrrole-5-carboxylate

Reaction equation

[H-].[Na+].[S:3]1[C:10]2[CH:9]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:7][C:6]=2[CH:5]=[CH:4]1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:20]Br>>[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:20][N:7]1[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][C:10]2[S:3][CH:4]=[CH:5][C:6]1=2

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 292163ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate

HCID 6397264-(Bromomethyl)-1,2-dichlorobenzene

Product 1

HCID 9798664Ethyl 4-(3,4-dichlorobenzyl)thieno[3,2-b]pyrrole-5-carboxylateYield 64%

Procedure

Sodium hydride (32 mg, 60%), was added to a solution of ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate (0.13 g) (from Preparation 4) and the reaction stirred for 30 minutes. 3,4-Dichlorobenzyl bromide (0.22 g) was added and stirring continued for a further 2 hours. The reaction was quenched by addition of water and extracted with ether. Combined organic extracts were dried (MgSO4) and concentrated and the residue purified by column chromatogaphy using isohexane-5% ethyl acetate as eluent to give the product as a yellow solid (0.15 g, 64%), NMR d(DMSO) 1.24 (3H, t), 4.22 (2H, q), 5.73 (2H, s), 6.63 (1H, d), 6.98 (1H, dd), 7.25 (2H, m), 7.37 (1H, s), 7.55 (1H, d); M/z (+) 354 (M+), 214, 158, 129.