Water → HCID 58573660, compound

HRID 931942Notes

Reaction equation

HRID 931942 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)[CH2:13][CH2:14][CH:15]=[CH2:16])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[BH4-].[Na+].O>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([CH:12]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)[CH2:13][CH2:14][CH:15]=[CH2:16])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 67999253HCID 67999253, compound

Product 1

HCID 58573660HCID 58573660, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a yellow slurry of 6-chloro-3-(1-(3-chlorophenyl)pent-4-enylidene)indolin-2-one (Example 62, Step B) (12.81 g, 37.2 mmol) in MeOH (200 mL) at room temperature was slowly added sodium borohydride (1.689 g, 44.7 mmol). Evolution of gas was observed. The yellow reaction mixture was stirred at room temperature for 30 min. Additional sodium borohydride (1.689 g, 44.7 mmol) was slowly added and the reaction mixture was stirred at room temperature for 1 h. The reaction mixture was poured into water (200 mL). A precipitate formed and the mixture was sonicated for 15 min then filtered. The filtrate was concentrated under reduced pressure to 36 mL and then extracted with EtOAc twice. The organic layers were combined, dried over Na2SO4 and concentrated under reduced pressure to provide the title compound.

Workup

  1. customat room temperature
  2. stirringthe reaction mixture was stirred at room temperature for 1 h
  3. customA precipitate formed
  4. customthe mixture was sonicated for 15 min
  5. filtrationthen filtered
  6. concentrationThe filtrate was concentrated under reduced pressure to 36 mL
  7. extractionextracted with EtOAc twice
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bf3c42e2a8b3428c8d3b6b0a151dc98c
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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