HCID 58679114, compound → HCID 58679068, compound

HRID 1442530Notes

Reaction equation

HRID 1442530 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[C:23]1[NH:27][C:26]2[CH:28]=[C:29]([C:31]([O:33][CH3:34])=[O:32])[S:30][C:25]=2[C:24]=1[CH:35]1[CH2:40][CH2:39][CH2:38][CH:37]=[CH:36]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.O1CCCC1.[OH-].[OH-].[Pd+2]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[C:23]1[NH:27][C:26]2[CH:28]=[C:29]([C:31]([O:33][CH3:34])=[O:32])[S:30][C:25]=2[C:24]=1[CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 58679114HCID 58679114, compound

Product 1

HCID 58679068HCID 58679068, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-(2,4-bisbenzyloxyphenyl)-6-(cyclohex-2-enyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate in a mixture of methanol (6 ml) and tetrahydrofuran (16 ml) was added 20% palladium hydroxide/carbon (400 mg, 0.74 mmol). After stirring for 13 hr under hydrogen atmosphere (3.4 atm) at room temperature, the reaction mixture was filtered through celite, and the filtrate was concentrated. The precipitated solid was collected by filtration. The solid was washed with diisopropyl ether (5 ml×3), and dried under reduced pressure to give methyl 5-(2,4-bisbenzyloxyphenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (1.12 g, yield 82%).

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. filtrationThe precipitated solid was collected by filtration
  4. washThe solid was washed with diisopropyl ether (5 ml×3)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-e8393ea2153841c9b50599a3fa48cf6c
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

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