6-Chloroindole → 6-Chloro-2,3-dihydro-1h-indole

HRID 556471Notes

Reaction equation

HRID 556471 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1>C(O)(C(F)(F)F)=O>[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][NH:10]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 871116-ChloroindoleHCID 4311764Sodium borohydride

Product 1

HCID 2585676-Chloro-2,3-dihydro-1h-indoleYield 59.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Sodium borohydride (2.0 g, 53 mmol) (Aldrich) was added in small portions to a mixture of 6-Chloro-1H-indole (1.0 g, 6.6 mmol) (Aldrich) in TFA (10 mL), which was cooled in ice-water bath, at such a rate that gas evolution was not too vigorous. When the addition was complete, the mixture was allowed to warm to room temperature and stirred overnight. The resulting mixture was concentrated in vacuo and the residue was dissolved in DCM. The organic layer was washed with Na2CO3 solution, dried with Na2SO4, and concentrated to give 0.6 g crude 6-Chloro-2,3-dihydro-1H-indole. MS: [M+H]+=154

Workup

  1. additionWhen the addition
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in DCM
  4. washThe organic layer was washed with Na2CO3 solution
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-67e64eeb4c6e4eb5947c7734da1a977a
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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