Oxalyl chloride → 1-(Cyclohexylmethyl)-7-methoxyindole-3-carbonyl chloride

HRID 968637Notes

Reaction equation

HRID 968637 reaction equation
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([C:19]([OH:21])=O)=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C([Cl:25])=O>C1COCC1>[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([C:19]([Cl:25])=[O:21])=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 686950531-(Cyclohexylmethyl)-7-methoxyindole-3-carboxylic acid

Product 1

HCID 859058491-(Cyclohexylmethyl)-7-methoxyindole-3-carbonyl chlorideYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(cyclohexylmethyl)-7-methoxyindole-3-carboxylic acid (2.5 g, 8.8 mmol) in THF (30 ml) was added oxalyl chloride (4.5 g, 35.3 mmol), dropwise with stirring. The mixture was stirred at room temperature for 18 h. The volatile components were evaporated under reduced pressure to afford 1-(cyclohexylmethyl)-7-methoxyindole-3-carbonyl chloride (2.7 g) as a crystalline solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 h
  2. customThe volatile components were evaporated under reduced pressure

Sources & evidence

ORD record
ord-af31ea58d986444ca2e570dd23ae8857
Source dataset
uspto-grants-2007_12
Patent number
US07304064B2

Reaction notes

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