Ammonia → HCID 57800076, compound

HRID 2278643Notes

Reaction equation

HRID 2278643 reaction equation
C([BH3-])#N.[Na+].[CH3:5][C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([C:15]([F:18])([F:17])[F:16])[CH:11]=[CH:10][CH:9]=2.N>C(O)(=O)C>[CH3:5][CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:15]([F:17])([F:16])[F:18])[NH:7]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5003444Sodium cyanoborohydrideHCID 196970222-methyl-4-(trifluoromethyl)-1H-indole

Product 1

HCID 57800076HCID 57800076, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

209 mg of 95% sodium cyanoborohydride are added to a solution of 210 mg of 2-methyl-4-trifluoromethyl-1H-indole in 8 ml of acetic acid, cooled to 15° C. The reaction mixture is stirred for 16 hours at ambient temperature and then poured into an aqueous ammonia solution (pH=9). The aqueous phase is extracted with methylene chloride and the combined organic phases are washed with a saturated sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure, so as to give 196 mg of 2-methyl-4-trifluoromethyl-2,3-dihydro-1H-indole in the form of a pale yellow liquid, which is used in the next step.

Workup

  1. extractionThe aqueous phase is extracted with methylene chloride
  2. washthe combined organic phases are washed with a saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7ef556d413764db68f032b347f2c8c8f
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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