Trifluoroacetic acid → 1-Methylindoline-5-carboxylic acid

HRID 1393672Notes

Reaction equation

HRID 1393672 reaction equation
C([SiH](CC)CC)C.[CH3:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH:16]=2)[CH:11]=[CH:10]1.FC(F)(F)C(O)=O>ClCCl>[CH3:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 70156011-Methyl-1H-indole-5-carboxylic acid

Product 1

HCID 230920021-Methylindoline-5-carboxylic acidYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dichloromethane (2 ml) and triethylsilane (1 ml) were added to 1-methyl-1H-indole-5-carboxylic acid (100 mg). The mixture was cooled to 0° C., trifluoroacetic acid (1 ml) was added dropwise thereto, and the mixture was warmed to room temperature and stirred for 2 hours. The reaction mixture was concentrated under reduced pressure, and precipitate was collected by filtration. The precipitate was washed with ether and dried under reduced pressure to give the title compound (66 mg, Y.:65%).

Workup

  1. temperaturethe mixture was warmed to room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and precipitate
  3. filtrationwas collected by filtration
  4. washThe precipitate was washed with ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-7ae5d4a85d124e04a59aa672b7dd4228
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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