Trifluoroacetic anhydride → Methyl 6-amino-1H-indole-2-carboxylate

HRID 1883118Notes

Reaction equation

HRID 1883118 reaction equation
C(OC([NH:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([C:18]([O:20][CH3:21])=[O:19])[NH:15]2)=[CH:11][CH:10]=1)=O)(C)(C)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[NH2:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([C:18]([O:20][CH3:21])=[O:19])[NH:15]2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 23510173methyl 6-(tert-butoxycarbonylamino)-1H-indole-2-carboxylate

Product 1

HCID 22060206Methyl 6-amino-1H-indole-2-carboxylateYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 551 mg methyl 6-[(tert-butoxycarbonyl)amino]-1H-indole-2-carboxylate dissolved in 15 mL dichloromethane was added 5 mL trifluoroacetic anhydride, and the mixture stirred at room temperature for 1.5 h. P The mixture was partitioned between dichloromethane and 1 N sodium hydroxide until neutral, dried over magnesium sulfate and concentrated. Obtained 360 mg of the crude methyl 6-amino-1H-indole-2-carboxylate. To 200 mg (1.05 mmol) of crude product dissolved in 5 mL dichloromethane and 340 □L pyridine at 0° C. was added 81 □L methanesulfonyl chloride. The mixture was stirred at 0° C. for 1 h, was partitioned between dichloromethane and 1 N hydrochloric acid until neutral, was dried over magnesium sulfate and concentrated to obtain 333 mg of methyl 6-[(methylsulfonyl)amino]-1H-indole-2-carboxylate as crude product.

Workup

  1. customP The mixture was partitioned between dichloromethane and 1 N sodium hydroxide until neutral,
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5158d72a422e4b8493daec38adc328ea
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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