Water → 5-(trifluoromethyl)-2,3-dihydro-1H-indole

HRID 427726Notes

Reaction equation

HRID 427726 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.C([BH3-])#N.[Na+].O.[OH-].[Na+]>C(O)(=O)C>[F:13][C:2]([F:1])([F:12])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 27630755-(trifluoromethyl)-1H-indoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 154477895-(trifluoromethyl)-2,3-dihydro-1H-indoleYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Trifluoromethylindole (D5, 1.0 g, 0.0057 mole) in glacial acetic acid (25 ml) was treated with sodium cyanoborohydride (1.7 g, 0.027 mole) under argon and stirred at room temperature for 2 hours. The mixture was poured into water (200 ml), basified with 40% aqueous sodium hydroxide solution, extracted into DCM, dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 20% ethyl acetate/60-80° petroleum ether to afford the title compound (0.45 g, 45%) as a pale yellow oil.

Workup

  1. extractionextracted into DCM
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with 20% ethyl acetate/60-80° petroleum ether

Sources & evidence

ORD record
ord-f8d37cd7232d431c9a830344053fb51a
Source dataset
uspto-grants-2001_11
Patent number
US06313145B1

Reaction notes

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