2-Acetoxybenzoyl chloride → 5-(2-Acetoxy-benzoylamino)-1-methyl-1H-indole-2-carboxylic acid ethyl ester

HRID 490009Notes

Reaction equation

HRID 490009 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([NH2:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2].C(N(C(C)C)CC)(C)C.[C:26]([O:29][C:30]1[C:31](=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:32](Cl)=[O:33])(=[O:28])[CH3:27]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([NH:15][C:32](=[O:33])[C:31]1[CH:35]=[CH:36][CH:37]=[CH:38][C:30]=1[O:29][C:26](=[O:28])[CH3:27])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 796682-Acetoxybenzoyl chlorideHCID 81531DiisopropylethylamineHCID 11424506Ethyl 5-amino-1-methyl-1H-indole-2-carboxylate

Product 1

HCID 691950055-(2-Acetoxy-benzoylamino)-1-methyl-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-amino-1-methyl-indole-2-carboxylic acid ethyl ester (12.86 g, 58.92 mM) and diisopropylethylamine (20.5 mL, 117.84 mM) in CH2Cl2 at 0° C. was added a solution of acetyl salicyloyl chloride in CH2Cl2 over 30 minutes. After the addition was complete the cooling bath was removed and the mixture was allowed to warm to room temperature and stirred at that temperature for 2 hours. The mixture was transferred to a separatory funnel and the solution was washed with 1N HCl (150 mL) and aqueous NaHCO3. The organic fraction was dried over MgSO4 and filtered. The solvent was removed under reduced pressure to provide the title compound.

Workup

  1. additionAfter the addition
  2. customwas removed
  3. customThe mixture was transferred to a separatory funnel
  4. washthe solution was washed with 1N HCl (150 mL) and aqueous NaHCO3
  5. dry with materialThe organic fraction was dried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a1c6d3c2d08f40a8b7c7b29d899c9b0a
Source dataset
uspto-grants-2005_12
Patent number
US06979692B2

Reaction notes

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