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Sodium hydride → methyl 4-(2-tert-butoxy-2-oxoethyl)-6-cyclohexyl-5-(4-chlorophenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 505811
Notes
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Reaction equation

HRID 505811 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[S:15][C:10]=3[C:9]=2[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]>CN(C=O)C.CCOC(C)=O>[C:33]([O:32][C:30](=[O:31])[CH2:29][N:12]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[C:9]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:10]2[S:15][C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][C:11]1=2)([CH3:36])([CH3:35])[CH3:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 68472408methyl 5-(4-chlorophenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 68467870methyl 4-(2-tert-butoxy-2-oxoethyl)-6-cyclohexyl-5-(4-chlorophenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylateYield 93%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

A solution (0.2 M) of methyl 5-(4-chlorophenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (prepared as described in example 13, step 4) in DMF was treated with NaH (2 eq., 60% dispersion in mineral oil), and the suspension was stirred at RT for 30 min, then tert-butyl bromoacetate (3 eq.) was added. The reaction mixture was heated at 50° C. for 2 h then cooled down and diluted with AcOEt. The organic phase was washed sequentially with aqueous HCl (1 N), aqueous NaHCO3 (saturated solution) and brine and dried. Evaporation of the solvent gave a residue that was purified by flash chromatography on silica gel (1:9 AcOEt/petroleum ether) to afford the title compound (93%).

Workup

  1. temperatureThe reaction mixture was heated at 50° C. for 2 h
  2. temperaturethen cooled down
  3. washThe organic phase was washed sequentially with aqueous HCl (1 N), aqueous NaHCO3 (saturated solution) and brine
  4. customdried
  5. customEvaporation of the solvent
  6. customgave a residue that
  7. customwas purified by flash chromatography on silica gel (1:9 AcOEt/petroleum ether)

Sources & evidence

ORD record
ord-0293b1a5392147a4b1759ac741c500f9
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07781431B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes