Hydrochloric Acid → HCID 58386464, compound

HRID 74544Notes

Reaction equation

HRID 74544 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)[CH:5]2[CH3:13].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][CH:5]2[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6331BoraneHCID 58386742HCID 58386742, compound

Product 1

HCID 58386464HCID 58386464, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

Under an argon atmosphere 1.6 g (8.7 mmol) 5,6-difluoro-3-methyl-1,3-dihydro-indol-2-one were placed in 50 mL THF. 18 mL (18 mmol) 1 M borane in THF were slowly added dropwise. The reaction mixture was stirred for 2 h at 70° C. After cooling to RT 10 mL methanol and 30 mL semiconc. HCl were successively added dropwise and then the mixture was refluxed for 1 h. After cooling to RT it was extracted with EtOAc. The aqueous phase was made alkaline with 4M NaOH solution and extracted with DCM. The organic phase was dried, filtered and evaporated down.

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. temperatureAfter cooling to RT it
  3. extractionwas extracted with EtOAc
  4. extractionextracted with DCM
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. customevaporated down

Sources & evidence

ORD record
ord-80e9dd36963144dd9a7ac1192b410d2a
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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