Water → 7-Fluoro-2,3-dihydro-3,3-dimethyl-1H-indole

HRID 2110345Notes

Reaction equation

HRID 2110345 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=O)[C:7]2([CH3:13])[CH3:12].COCCO[AlH2-]OCCOC.[Na+].[OH-].[Na+].O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH2:8][C:7]2([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 119764367-fluoro-3,3-dimethyloxindoleHCID 16684438Red-Al

Product 1

HCID 451422257-Fluoro-2,3-dihydro-3,3-dimethyl-1H-indoleYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7-fluoro-3,3-dimethyloxindole (EXAMPLE 99, step 5, 2.24 g 12.5 mmol) in toluene (15 mL) under nitrogen was heated at 80° C. Vitride (65 wt % in toluene, 6 mL, 19.3 mmol) was added dropwise via an addition funnel. The resulting solution was stirred at 80° C. for an additional 1.5 hours, then cooled in an ice bath. Aqueous sodium hydroxide solution (1N, 15 mL) was added slowly to quench the reaction. Water (15 mL) was added and the reaction mixture was extracted with ethyl acetate (20 mL). The organic layer was washed with brine, dried (anhydrous sodium sulfate), filtered through a pad of silica gel, and concentrated under reduced pressure to yield 1.68 g (82%) of 7-fluoro-3,3-dimethylindoline as a colorless oil. MS (ES) m/z 166.1 ([M+H]+); HRMS: calcd for C10H12FN+H+, 166.1032; found (ESI, [M+H]+), 166.1040.

Workup

  1. temperaturecooled in an ice bath
  2. customto quench
  3. customthe reaction
  4. extractionthe reaction mixture was extracted with ethyl acetate (20 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried (anhydrous sodium sulfate)
  7. filtrationfiltered through a pad of silica gel
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b55913cc8804512b04db2b23517ba18
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

Loading…