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

HRID 505826Notes

Reaction equation

HRID 505826 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([C:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]=2)[C:10]2[CH:25]=[C:26]([C:28]([O:30][CH3:31])=[O:29])[S:27][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[C:10]2[CH:25]=[C:26]([C:28]([O:30][CH3:31])=[O:29])[S:27][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 68467568methyl 6-benzyl-4-cyclohex-1-en-1-yl-5-phenyl-6H-thieno[2,3-b]pyrrole-2-carboxylate

Product 1

HCID 11441793methyl 6-benzyl-4-cyclohexyl-5-phenyl-6H-thieno[2,3-b]pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

A solution (0.7 M) of methyl 6-benzyl-4-cyclohex-1-en-1-yl-5-phenyl-6H-thieno[2,3-b]pyrrole-2-carboxylate in TFA at 0° C. was treated with triethylsilane (1.5 eq.). The mixture was stirred at 0° C. for 1 h then concentrated to give a residue that was purified by flash chromatography on silica gel (1:30 acetone/toluene) affording methyl 6-benzyl-4-cyclohexyl-5-phenyl-6H-thieno[2,3-b]pyrrole-2-carboxylate as a solid that was dissolved in THF/MeOH (1:1). The resulting solution (0.04 M) was treated with aqueous KOH (1 N solution, 4 eq.) then the mixture was heated to 80° C. for 4 h. After cooling down, the mixture was concentrated then the resulting residue was diluted with water and pH was turned to neutral value by addition of aqueous ammonium chloride (saturated solution). The mixture was concentrated to give a residue that was purified by RP-HPLC (Conditions: Waters X-TERRA MS C18, 10 micron, 10×150 mm; flow: 20 mL/min; Gradient: A: H2O+0.05% TFA; B: MeCN+0.05% TFA; 50% A isocratic for 2 min then linear to 0% A in 10 min) to afford the title compound (58%) as a solid.

Workup

  1. concentrationthen concentrated
  2. customto give a residue that
  3. customwas purified by flash chromatography on silica gel (1:30 acetone/toluene)

Sources & evidence

ORD record
ord-76094b2f22074027acf6eb6ba540df58
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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