Dimethylformamide → methyl 3-[1-(phenoxyacetyl)-2,3-dihydro-1H-pyrrol-3-yl]benzoate

HRID 2275651Notes

Reaction equation

HRID 2275651 reaction equation
N1(C(OC[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)CC=CC1.Br[C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20]([O:22][CH3:23])=[O:21].[C:27]([O-:30])(=O)C.[K+].[CH3:32][N:33]([CH3:36])[CH:34]=[O:35].[CH3:37][CH2:38]OC(C)=O>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[O:30]([CH2:27][C:34]([N:33]1[CH:36]=[CH:38][CH:37]([C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=2)[C:20]([O:22][CH3:23])=[O:21])[CH2:32]1)=[O:35])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 12070Methyl 3-bromobenzoateHCID 517044Potassium AcetateHCID 643471Benzyl 3-pyrroline-1-carboxylate

Product 1

HCID 66662462methyl 3-[1-(phenoxyacetyl)-2,3-dihydro-1H-pyrrol-3-yl]benzoate

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

A solution of benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate (0.626 mL, 0.00349 mol), methyl 3-bromo-benzoate (300 mg, 0.001 mol), palladium(II) diacetate (14 mg, 0.000063 mol), potassium acetate (356 mg, 0.00363 mol), and tetra-N-butylammonium bromide (4.50×10−2 mg, 0.00140 mol) in N,N-dimethylformamide (5 mL, 0.06 mol) was stirred under nitrogen at 40° C. for 4 days. The reaction mixture was diluted with AcOEt and water. The organic layer was separated and the aqeous layer was extracted with AcOEt. The combined organic layer was washed with brine, dryed with MgSO4, and concentrated to afford the crude product. The crude product was purified by flash chromatography, eluting with 30% AcOEt in hexanes.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqeous layer was extracted with AcOEt
  3. washThe combined organic layer was washed with brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f7977220354b4447b328602b0920536c
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

Loading…