Acetyl chloride → methyl 3-acetyl-6-chloro-1H-indole-5-carboxylate

HRID 1891018Notes

Reaction equation

HRID 1891018 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].[Cl-].C([Al+]CC)C.[C:21](Cl)(=[O:23])[CH3:22]>ClCCl>[C:21]([C:6]1[C:5]2[C:9](=[CH:10][C:2]([Cl:1])=[C:3]([C:11]([O:13][CH3:14])=[O:12])[CH:4]=2)[NH:8][CH:7]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 10727132Methyl 6-chloro-1H-indole-5-carboxylateHCID 16686102Diethyl aluminum chloride

Product 1

HCID 67774875methyl 3-acetyl-6-chloro-1H-indole-5-carboxylateYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 6-chloro-1H-indole-5-carboxylate (0.5 g, 2.4 mmol) in dichloromethane at 0 C, was added drop-wise, a solution of diethyl aluminum chloride (3.6 mL, 1M) and stirred under nitrogen for 45 min. To this mixture, added a solution of acetyl chloride (0.3 g, 3.8 mmol) in dichloromethane (3 mL). The resulting mixture was stirred for 3 h and at room temperature for 30 min. The reaction was quenched by the addition of cold Tris buffer (pH 7.5, 1 mM and added dichloromethane (2×15 mL). The solid that separated was removed by filtration, washed with water and dried to give the title compound (0.44 g, 73%), m/z=252 (M+H).

Workup

  1. customThe reaction was quenched by the addition of cold Tris buffer (pH 7.5, 1 mM
  2. additionadded dichloromethane (2×15 mL)
  3. customThe solid that separated
  4. customwas removed by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-5b790471c30e4abc95eabbc8c0d75754
Source dataset
uspto-grants-2013_08
Patent number
US08507499B2

Reaction notes

Loading…