Sodium Hydroxide → HCID 21717319, compound

HRID 1386055Notes

Reaction equation

HRID 1386055 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:9]([CH3:13])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[CH3:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:16]=1[CH:17]=O.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH3:12][C:10]1[N:11]=[C:3]2[C:2]([NH:1][CH2:17][C:16]3[C:19]([CH3:23])=[CH:20][CH:21]=[CH:22][C:15]=3[CH3:14])=[CH:7][C:6]([F:8])=[CH:5][N:4]2[C:9]=1[CH3:13]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 5838412,6-DimethylbenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 217173636-Fluoro-2,3-dimethylimidazo[1,2-a]pyridin-8-amine

Product 1

HCID 21717319HCID 21717319, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

A stirred mixture of 8-amino-2,3-dimethyl-6-fluoroimidazo[1,2-a]pyridine (0.16 g, 0.89 mmol), zinc(II) chloride (0.14 g, 1.04 mmol) and 2,6-dimethylbenzaldehyd (0.14 g, 1.04 mmol) in methanol (50 ml) was treated with sodium cyanoborohydride (0.065 g, 1.04 mmol) and was refluxed for 7 h. The cooled reaction mixture was added to 0.5 M NaOH (20 ml) and the precipitated solids were filtered off and purified by column chromatography on silica gel, using methanol:methylene chloride (1:10) as eluent. Crystallization from petroleum ether gave 0.1 g (38%) of the title compound.

Workup

  1. temperaturewas refluxed for 7 h
  2. customThe cooled reaction mixture
  3. filtrationthe precipitated solids were filtered off
  4. custompurified by column chromatography on silica gel
  5. customCrystallization from petroleum ether

Sources & evidence

ORD record
ord-b2cd7356c9754d1fa556ee2c23b34d0f
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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