Triethylsilane → methyl 6-cyclohexyl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 505779Notes

Reaction equation

HRID 505779 reaction equation
[C:1]1([C:7]2[C:8]3[S:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][C:9]=3[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH:1]1([C:7]2[C:8]3[S:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][C:9]=3[NH:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 11559121methyl 6-cyclohex-1-en-1-yl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 68467632methyl 6-cyclohexyl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

A solution (0.1 M) of methyl 6-cyclohex-1-en-1-yl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate in TFA at 0° C. was treated with triethylsilane (1.5 eq.). The reaction mixture was stirred at 0° C. for 1 h then solvent was evaporated to give the title compound (95%) as a solid.

Workup

  1. customsolvent was evaporated

Sources & evidence

ORD record
ord-18e2077e16f34f598996e4aef97bf6c0
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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