4-Fluorobenzoyl chloride → HCID 59625766, compound

HRID 401673Notes

Reaction equation

HRID 401673 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=2)[CH:13]=[CH:12]1.[Cl-].C([Al+]CC)C>ClCCCl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:13]2[C:14]3[C:19](=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=3)[NH:11][CH:12]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 639844Methyl indole-6-carboxylateHCID 16686102Diethyl aluminum chloride

Product 1

HCID 59625766HCID 59625766, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of 4-fluorobenzoyl chloride 43b (2 mmol, 0.24 mL) in 8 mL of DCE was added dropwise to an ice-cold solution of methyl 1H-indole-6-carboxylate 43a (1.43 mmol, 250 mg) and diethylaluminum chloride (1 M in hexanes, 1.86 mmol, 1.86 mL) in 8 mL of DCE. After 2 h at 0° C., the mixture was warmed to room temperature and was stirred overnight. To the mixture was added pH 7 buffer; the resulting solid was filtered and washed with CH2Cl2 to give 162 mg (38%) of methyl 3-(4-fluorobenzoyl)-1H-indole-6-carboxylate 43c. MS m/z (M+H+) 298.0.

Workup

  1. additionTo the mixture was added pH 7 buffer
  2. filtrationthe resulting solid was filtered
  3. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-8d06208fdb1840d1b7fe53c286515cda
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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