4,4'-Dibromobiphenyl → Ethyl (3ar,6ar)-1-(4'-bromo-1,1'-biphenyl-4-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1h)-carboxylate

HRID 1947389Notes

Reaction equation

HRID 1947389 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:21]1[CH2:25][CH2:24][C@@H:23]2[CH2:26][N:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:28][C@H:22]12>ClCCl>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:21]3[CH2:25][CH2:24][C@@H:23]4[CH2:26][N:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:28][C@H:22]34)=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 71104,4'-DibromobiphenylHCID 10796Cesium carbonateHCID 24743918(3AR,6AR)-5-Ethoxycarbonyl-1H-hexahydropyrrolo[3,4-B]pyrrole

Product 1

HCID 67397057Ethyl (3ar,6ar)-1-(4'-bromo-1,1'-biphenyl-4-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1h)-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

The catalyst solution was added to the vessel containing the 4,4′-dibromobiphenyl, cesium carbonate, and the product of Example 41C and the mixture was heated to 98° C. for 12 hours. The mixture was cooled to 20° C. and 80 g of dichloromethane was added. The resulting mixture was stirred and then filtered to remove the catalyst. The resulting solution was concentrated under reduced pressure and the residue was purified by column chromatography to yield 5.65 g of the title compound.

Workup

  1. additionThe catalyst solution was added to the vessel
  2. filtrationfiltered
  3. customto remove the catalyst
  4. concentrationThe resulting solution was concentrated under reduced pressure
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5e9959faad2b4997bcd71b1aa74fc6e8
Source dataset
uspto-grants-2013_03
Patent number
US08399468B2

Reaction notes

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