Sodium borohydride → HCID 67114885, compound

HRID 1408512Notes

Reaction equation

HRID 1408512 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([C:15](OC)=[O:16])=[CH:13][C:12]([C:19]([F:22])([F:21])[F:20])=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+]>C1COCC1.CO.O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([CH2:15][OH:16])=[CH:13][C:12]([C:19]([F:22])([F:21])[F:20])=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 67114960HCID 67114960, compound

Product 1

HCID 67114885HCID 67114885, compoundYield 92.5%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Intermediate 18 (0.662 g, 2.1 mmol) dissolved in a mixture of THF (5 ml) and MeOH (5 ml) and added sodium borohydride (79 mg, 2.1 mmol). Colour of the reaction mixture changed to pink and then two drops of water added to it. Reaction mixture allowed to stir at rt for 1 h and at this stage colour changed to pink to pale yellow. Reaction mixture was allowed to stir further overnight. Work up (AcOEt/H2O) and evaporation of organic layer on vacuum afforded the title compound (558 mg) as a white solid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.42 (d, J 8.9, 2H), 8.01 (d, J 8.9, 2H), 7.01 (s, 1H), 5.77 (t, J 5.4, 1H), 4.63 (d, J 5.4, 2H).

Workup

  1. additionadded to it
  2. customReaction mixture
  3. customReaction mixture
  4. stirringto stir further overnight
  5. custom(AcOEt/H2O) and evaporation of organic layer on vacuum

Sources & evidence

ORD record
ord-787d37982d46411db3a27b8512485fd2
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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