Allyl bromide → methyl 4-allyl-6-cyclohexyl-5-(2-vinylphenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 1008977Notes

Reaction equation

HRID 1008977 reaction equation
[CH:1]1([C:7]2[C:8]3[S:22][C:21]([C:23]([O:25][CH3:26])=[O:24])=[CH:20][C:9]=3[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:18]=[CH2:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:29](Br)[CH:30]=[CH2:31]>CN(C=O)C>[CH2:31]([N:10]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:18]=[CH2:19])=[C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:8]2[S:22][C:21]([C:23]([O:25][CH3:26])=[O:24])=[CH:20][C:9]1=2)[CH:30]=[CH2:29]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 67298999methyl 6-cyclohexyl-5-(2-vinylphenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 67298543methyl 4-allyl-6-cyclohexyl-5-(2-vinylphenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0.1M solution of methyl 6-cyclohexyl-5-(2-vinylphenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate in dry DMF, 60% NaH (1.2 eq.) in mineral oil was added; when gas evolution had ceased, allyl bromide (1.3 eq.) was added, and the suspension was stirred at RT for 1 h. All volatiles were evaporated and the title compound was isolated by chromatography (PE/Et2O 20:1). Yield: 98%. 1H-NMR (400 MHz, CDCl3, 300K, δ) 7.73 (d, 1H, J 7.6), 7.70 (s, 1H), 7.47 (t, 1H, J 7.6), 7.36 (t, 1H, J 7.6), 7.25 (d, 1H, J 7.6), 6.48 (dd, 1H, J 17.8, 11.4), 5.72 (d, 1H, J 17.8), 5.80-5.69 (m, 1H), 5.20 (d, 1H, J 11.4), 5.09 (dd, 1H, J 10.3, 1.1), 4.97 (dd, 1H, J 17.1, 1.1), 4.36 (dd, 1H, J 16.2, 5.6), 4.23 (dd, 1H, J 16.2, 5.6), 3.92 (s, 3H), 2.35-2.24 (m, 1H), 1.75-1.16 (m, 10H).

Workup

  1. customAll volatiles were evaporated

Sources & evidence

ORD record
ord-e2568ab551064410acfb7d77ab2463ec
Source dataset
uspto-grants-2011_07
Patent number
US07973026B2

Reaction notes

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