Benzyl Bromide → 4-Benzyl-6-cyclohexyl-5-phenyl-thieno[3,2-b]pyrrole-2-carboxylic acid

HRID 505783Notes

Reaction equation

HRID 505783 reaction equation
[CH:1]1([C:7]2[C:8]3[S:20][C:19]([C:21]([O:23]C)=[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][CH2:2]1.[H-].[Na+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C.CCOCC.O>[CH2:27]([N:10]1[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:8]2[S:20][C:19]([C:21]([OH:23])=[O:22])=[CH:18][C:9]1=2)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 68467632methyl 6-cyclohexyl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 111659334-Benzyl-6-cyclohexyl-5-phenyl-thieno[3,2-b]pyrrole-2-carboxylic acidYield 22%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution (0.15 M) of methyl 6-cyclohexyl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate in DMF at 0° C. was treated with NaH (3.5 eq., 60% dispersion in mineral oil), and the suspension was stirred at RT for 30 min then it was treated with benzyl bromide (2.5 eq.). The reaction mixture was stirred at RT for 3 h then it was diluted with Et2O and water then the layers were separated and the aqueous phase was extracted with AcOEt. The combined organic phase was dried and concentrated giving a residue that was purified by flash chromatography on silica gel (1:10 MeOH/DCM) affording the title compound (22%) as a solid.

Workup

  1. stirringThe reaction mixture was stirred at RT for 3 h
  2. customthe layers were separated
  3. extractionthe aqueous phase was extracted with AcOEt
  4. customThe combined organic phase was dried
  5. concentrationconcentrated
  6. customgiving a residue that
  7. customwas purified by flash chromatography on silica gel (1:10 MeOH/DCM)

Sources & evidence

ORD record
ord-61257cf5fa1a46da82c7227d83a23c8d
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

Loading…