Cesium carbonate → (3aS,6aS)-ethyl-1-(3-(3-fluorophenylsulfonyl)quinolin-8-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

HRID 2068145Notes

Reaction equation

HRID 2068145 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[N:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][C:15]=3I)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[NH:22]1[CH2:26][CH2:25][C@H:24]2[CH2:27][N:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:29][C@@H:23]12.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:33]([O:32][C:30]([N:28]1[CH2:27][C@H:24]2[C@H:23]([N:22]([C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:14]=3[N:13]=[CH:12][C:11]([S:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)(=[O:10])=[O:9])=[CH:20]4)[CH2:26][CH2:25]2)[CH2:29]1)=[O:31])[CH3:34]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 43604250(3AS,6AS)-5-Ethoxycarbonyl-1H-hexahydropyrrolo[3,4-B]pyrroleHCID 673141573-(3-Fluorophenylsulfonyl)-8-iodoquinoline

Product 1

HCID 68770827(3aS,6aS)-ethyl-1-(3-(3-fluorophenylsulfonyl)quinolin-8-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylateYield 93.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

0.255 of g 3-(3-fluorophenylsulfonyl)-8-iodoquinoline (0.617 mmol), 0.114 g of (3aS,6aS)-ethyl hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate (0.617 mmol), 0.404 g of cesium carbonate (1.234 mmol), 0.014 g of palladium acetate (0.062 mmol) and 0.029 g of X-Phos (2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl, 0.062 mmol) in 5 mL toluene were stirred at 90° C. for 8 h. The reaction mixture was directly purified via silica gel chromatography (eluent toluene/methanol 10/1 +2.5% triethylamine). Fractions containing the product were combined and the solvent was evaporated to yield 0.271 g of the desired product which was used in example 26 without additional purification.

Workup

  1. customThe reaction mixture was directly purified via silica gel chromatography (eluent toluene/methanol 10/1 +2.5% triethylamine)
  2. additionFractions containing the product
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d32bbb857baa443db54dba13e6587e2e
Source dataset
uspto-grants-2012_10
Patent number
US08293913B2

Reaction notes

Loading…