Hydrochloric Acid → HCID 67616430, compound

HRID 1467997Notes

Reaction equation

HRID 1467997 reaction equation
[F:1][C:2]1(F)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:9]=2)[NH:4][C:3]1=O.BF.Cl.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([S:11]([CH3:14])(=[O:12])=[O:13])[CH:9]=2)[NH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67609006HCID 67609006, compoundHCID 178419219HCID 178419219, compound

Product 1

HCID 67616430HCID 67616430, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring solution of 3,3-difluoro-5-(methylsulfonyl)indolin-2-one (1.0 g, 4.0 mmol) in anhydrous THF (25 mL), a solution of “BH2F.THF” (nominal concentration 1.3 M, 13 ml) was added at 0° C. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was brought to 0° C., aqueous HCl (3 M, 13 mL) was added dropwise. The reaction mixture was subsequently neutralized with aqueous NaOH (2.5M). The mixture was extracted with ethyl acetate, separated and concentrated in vacuo. The residue was purified by flash column chromatography to give the title compound (0.450 g, 52.3%); MS: 213.9 (M+1).

Workup

  1. customwas brought to 0° C.
  2. extractionThe mixture was extracted with ethyl acetate
  3. customseparated
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-694cece30b6548679b6ba73a532baa8c
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Reaction notes

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