N,N'-Dimethylethylenediamine → Ethyl 2-methyl-1-phenyl-1H-pyrrole-3-carboxylate

HRID 642212Notes

Reaction equation

HRID 642212 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][NH:8][C:7]=1[CH3:11])=[O:5])[CH3:2].I[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CNCCNC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][N:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]=1[CH3:11])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11575IodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 136747Ethyl 2-methyl-3-pyrrolecarboxylate

Product 1

HCID 15272135Ethyl 2-methyl-1-phenyl-1H-pyrrole-3-carboxylateYield 52.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Procedure

A solution of 2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (388 mg, 2.53 mmol), iodobenzene (619 mg, 3.04 mmol), copper(I) iodide (24 mg, 0.127 mmol), N,N′-dimethyl-ethane-1,2-diamine (54 μL, 0.506 mmol), potassium phosphate (1.128 g, 5.31 mmol) in dry toluene (2.5 mL) was irradiated with microwave at 130° C. for 2 h; then the solids were filtered off, the filtrate was concentrated, the resulted residue was purified on column to give the title product (302 mg); The title compound, 1H NMR (200 MHz, CDCl3): δ (ppm)=7.5-7.2 (m, 5H), 6.51 (s, 2H), 4.28 (q, 2H, J=7.4 Hz), 2.44 (s, 3H), 1.36 (t, 3H, J=7.4 Hz).

Workup

  1. filtrationthen the solids were filtered off
  2. concentrationthe filtrate was concentrated
  3. customthe resulted residue was purified on column

Sources & evidence

ORD record
ord-f5ab3ba5bde042e889bfdd5ba80252a8
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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