Dimethylformamide → 2-carbamoyl-6-benzyloxy-1H-indole

HRID 1246002Notes

Reaction equation

HRID 1246002 reaction equation
[C:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:7]=2)(O)=[O:2].C(Cl)(=O)C(Cl)=O.C[N:28](C=O)C.C([O-])(=O)C.[NH4+]>C(Cl)Cl>[C:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:7]=2)(=[O:2])[NH2:28]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 517165Ammonium AcetateHCID 51149926-(benzyloxy)-1H-indole-2-carboxylic acid

Product 1

HCID 219156812-carbamoyl-6-benzyloxy-1H-indoleYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-carboxy-6-benzyloxy-1H-indole (0.125 g; 0.468 mmol), oxalyl chloride (0.5 mmol) and DMF (0.2 ml) in CH2Cl2 was stirred at room temperature for 2 hours. After evaporation to dryness, the residue was redissolved in acetone; ammonium acetate (0.074 g; 0.95 mmol) was added to the solution and the mixture was stirred at room temperature for 1 hour. After evaporation, the residue was purified by flash chromatography eluting with CH2Cl2/acetone 80/20 to give 2-carbamoyl-6-benzyloxy-1H-indole.

Workup

  1. customAfter evaporation to dryness
  2. dissolutionthe residue was redissolved in acetone
  3. customAfter evaporation
  4. customthe residue was purified by flash chromatography
  5. washeluting with CH2Cl2/acetone 80/20

Sources & evidence

ORD record
ord-1c9dfdcda30a4d3497c21ae27af51a76
Source dataset
uspto-grants-2006_10
Patent number
US07125906B2

Reaction notes

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