Sodium cyanoborohydride → 1383974-37-5

HRID 2278658Notes

Reaction equation

HRID 2278658 reaction equation
C([BH3-])#N.[Na+].[F:5][CH:6]([F:17])[O:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[CH:11][NH:12]2>FC(F)(F)C(O)=O>[F:17][CH:6]([F:5])[O:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH2:10][CH2:11][NH:12]2

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 866992851315364-47-6

Product 1

HCID 866992831383974-37-5Yield 29.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

0.722 mg of sodium cyanoborohydride is added to a solution of 1 g of 4-difluoromethoxy-1H-indole in 15 ml of trifluoroacetic acid, cooled to 0° C., and the stirring is continued for 3 hours. The reaction mixture is then concentrated under reduced pressure, treated with a concentrated sodium hydroxide solution, extracted with dichloromethane, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica column chromatography, elution being carried out with a mixture of heptane and ethyl acetate (20/80: v/v), so as to give 300 mg of 4-difluoromethoxy-2,3-dihydro-1H-indole in the form of a yellow oil, the characteristics of which are the following:

Workup

  1. concentrationThe reaction mixture is then concentrated under reduced pressure
  2. additiontreated with a concentrated sodium hydroxide solution
  3. extractionextracted with dichloromethane
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica column chromatography, elution
  8. additionbeing carried out with a mixture of heptane and ethyl acetate (20/80: v/v)

Sources & evidence

ORD record
ord-4bb71e9b6e0d4e118bd5b6c79c75b6f8
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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