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

HRID 1017730Notes

Reaction equation

HRID 1017730 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

4

Reactant 3

HCID 24758Sodium hydrideHCID 292163ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylateHCID 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.

Workup

  1. stirringstirring
  2. waitcontinued for a further 2 hours
  3. customThe reaction was quenched by addition of water
  4. extractionextracted with ether
  5. dry with materialCombined organic extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. customthe residue purified by column chromatogaphy

Sources & evidence

ORD record
ord-382511cda3e04e19878d9355e56be42a
Source dataset
uspto-grants-2002_11
Patent number
US06479527B1

Reaction notes

Loading…