Hydrochloric Acid → 5,6-Difluoroindoline

HRID 1640259Notes

Reaction equation

HRID 1640259 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6](=O)[CH2:5]2.B.CO.Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6331BoraneHCID 125852825,6-Difluorooxindole

Product 1

HCID 167925945,6-Difluoroindoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

Under an argon atmosphere 0.30 g (1.8 mmol) 5,6-difluoroxindole were dissolved in 10 mL THF and 3.0 mL of a 1 molar borane solution in THF were added dropwise. Then the reaction mixture was heated to 70° C. for 2 h and then cooled. After mixing with 3 mL MeOH another 5 mL of a 4N aqueous hydrochloric acid solution were added and the mixture was refluxed for 1 h. The organic phase was evaporated down, the aqueous phase was washed with DCM and then made alkaline with a 4N aqueous sodium hydroxide solution and extracted several times with EtOAc. The combined organic phases were dried on sodium sulphate, filtered and evaporated down.

Workup

  1. temperaturecooled
  2. additionwere added
  3. temperaturethe mixture was refluxed for 1 h
  4. customThe organic phase was evaporated down
  5. washthe aqueous phase was washed with DCM
  6. extractionextracted several times with EtOAc
  7. customThe combined organic phases were dried on sodium sulphate
  8. filtrationfiltered
  9. customevaporated down

Sources & evidence

ORD record
ord-e29326c8089a46208e994291eb4a1279
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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