2-Formylphenylboronic acid → methyl 6-cyclohexyl-5-(2-formylphenyl)-4-(2-methoxy-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 1008982Notes

Reaction equation

HRID 1008982 reaction equation
Br[C:2]1[N:6]([CH2:7][C:8]([O:10][C:11](C)(C)C)=[O:9])[C:5]2[CH:15]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[S:17][C:4]=2[C:3]=1[CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[CH:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O)=[O:29].[F-].[K+]>O1CCOCC1.CC(P(C(C)(C)C)C(C)(C)C)(C)C.CC(P(C(C)(C)C)C(C)(C)C)(C)C.[Pd]>[CH:22]1([C:3]2[C:4]3[S:17][C:16]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][C:5]=3[N:6]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[C:2]=2[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[CH:28]=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 3

HCID 2921892-Formylphenylboronic acidHCID 522689Potassium FluorideHCID 67298685methyl 5-bromo-4-(2-tert-butoxy-2-oxoethyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 86629783methyl 6-cyclohexyl-5-(2-formylphenyl)-4-(2-methoxy-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylateYield 80%

Reagents, catalysts & solvents 2

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)CatalystHCID 312751,4-DioxaneSolvent

Procedure

Methyl 5-bromo-6-cyclohexyl-4-(2-methoxy-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate (prepared by analogy to Example 7, Step 2, substituting tert-butyl bromoacetate with methyl bromo acetate), 2-formyl benzene boronic acid (1.3 eq.), KF (3.2 eq.) and Pd(t-Bu3P)2 (0.2 eq.) were mixed in dioxane (0.1M). The mixture was degassed, flushed with nitrogen and left stirring for 5 h at RT. Then all volatiles were evaporated i. vac. and the residual material was isolated by chromatography (PE:EtOAc, 9:1). The product was obtained as a yellowish solid (80%). MS (ES+) m/z 440 (M+H)+.

Workup

  1. customThe mixture was degassed
  2. customflushed with nitrogen
  3. waitleft
  4. customThen all volatiles were evaporated i
  5. customand the residual material was isolated by chromatography (PE:EtOAc, 9:1)

Sources & evidence

ORD record
ord-c8d7eff7da9c4800bf89730a7aa52c70
Source dataset
uspto-grants-2011_07
Patent number
US07973026B2

Reaction notes

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