Sodium borohydride → HCID 21183722, compound

HRID 1384803Notes

Reaction equation

HRID 1384803 reaction equation
[BH4-].[Na+].[CH2:3]([N:5]1[C:13]2[CH:12]=[CH:11][C:10]([F:14])=[CH:9][C:8]=2[C:7]2[C:15]([C:26](OC)=[O:27])=[N:16][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:18](=[O:19])[C:6]1=2)[CH3:4]>O1CCCC1.CO>[CH2:3]([N:5]1[C:13]2[CH:12]=[CH:11][C:10]([F:14])=[CH:9][C:8]=2[C:7]2[C:15]([CH2:26][OH:27])=[N:16][N:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:18](=[O:19])[C:6]1=2)[CH3:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 21183743HCID 21183743, compound

Product 1

HCID 21183722HCID 21183722, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5.1 g (135 mmol) of sodium borohydride are added, in several portions and at room temperature, to a solution of 10 g (27.3 mmol) of methyl 5-ethyl-8-fluoro-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxylate in 200 ml of tetrahydrofuran and 5.8 ml of methanol and the mixture is stirred for 4 h at reflux. The mixture is poured onto an ice-cold 0.1N hydrochloric acid solution, an insoluble material is separated by filtration, the insoluble material being washed with water and with diethyl ether, on sintered glass, and then it is dried. 7.2 g (21.4 mmol) of compound are isolated in the form of a white solid which is used as is in the following stage.

Workup

  1. temperatureat reflux
  2. customan insoluble material is separated by filtration
  3. washthe insoluble material being washed with water and with diethyl ether, on sintered glass
  4. customit is dried

Sources & evidence

ORD record
ord-6935628ff86a4ac482c33753fca9d7be
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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