Indole → HCID 9859793, compound

HRID 260991Notes

Reaction equation

HRID 260991 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[N:1]1([C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([O:15][CH3:16])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 798IndoleHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11894Methyl 2-bromobenzoate

Product 1

HCID 9859793HCID 9859793, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of indole (4.16 g; 35.53 mmol), methyl 2-bromobenzoate (2.64 g; 35.53 mmol), potassium carbonate (5.50 g) and CuO (2.0 g) in 40 mL of DMF was refiuxed uncler an argon atmosphere for 3.5 hrs. The crude material obtained upon extraction into ethyl acetate and removal of the solvent was purified on a silica gel column (10% ethyl acetate/hexane) to obtain 4.20 g (47%) of methyl 2-(1-indolyl)benzoate, 1H NMR (CDCl3): δ 3.45 (s, 3H); 6.43 (d, 1H); 6.99-7.20 (m, 4H); 7.35-7.42 (m, 2H); 7.60 (m, 2H); 7.88 (d, 1H).

Workup

  1. customwas purified on a silica gel column (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b8989d4ab2354e81abfed5e1000a3560
Source dataset
uspto-grants-1996_06
Patent number
US05530157

Reaction notes

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