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

HRID 505809Notes

Reaction equation

HRID 505809 reaction equation
Br[C:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C:5]2[CH:14]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[S:16][C:4]=2[C:3]=1[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>CCO.C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:10]([O:9][C:7]([N:6]1[C:2]([C:31]2[CH:32]=[CH:33][C:28]([Cl:27])=[CH:29][CH:30]=2)=[C:3]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:4]2[S:16][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][C:5]1=2)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 433294Lithium ChlorideHCID 67298537methyl 5-bromo-4-(tert-butoxycarbonyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 68467133methyl 4-(tert-butoxycarbonyl)-5-(4-chlorophenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylateYield 69%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution (0.1 M) of methyl 5-bromo-4-(tert-butoxycarbonyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate in EtOH/toluene (1:1) was treated with 4-chlorophenylboronic acid (1.3 eq.) and LiCl (2 eq.). Aqueous Na2CO3 (2 N, 2.5 eq.) was added and the solution was degassed, then Pd(PPh3)4 (0.1 eq.) was added. The mixture was heated to 80° C. for 18 h, then cooled and diluted with AcOEt. The organic phase was washed sequentially with water, aqueous HCl (1 N) and brine, then dried and concentrated giving a residue that was purified by flash chromatography on silica gel (1:9 AcOEt/petroleum ether) to afford the title compound (69%) as a solid.

Workup

  1. customthe solution was degassed
  2. temperaturecooled
  3. washThe organic phase was washed sequentially with water, aqueous HCl (1 N) and brine
  4. customdried
  5. concentrationconcentrated
  6. customgiving a residue that
  7. customwas purified by flash chromatography on silica gel (1:9 AcOEt/petroleum ether)

Sources & evidence

ORD record
ord-23002f57d1f946539406bf88157d8f74
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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