Sodium Hydroxide → 2,3-Dimethyl-8-(2,6-diethylbenzylamino)-imidazo[1,2-a]pyridine

HRID 1386056Notes

Reaction equation

HRID 1386056 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:13]([C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][CH3:24])[C:16]=1[CH:17]=O)[CH3:14].[BH3-]C#N.[Na+].[OH-].[Na+]>CO.[Cl-].[Cl-].[Zn+2].CCCCCC>[CH3:11][C:9]1[N:10]=[C:3]2[C:2]([NH:1][CH2:17][C:16]3[C:15]([CH2:13][CH3:14])=[CH:22][CH:21]=[CH:20][C:19]=3[CH2:23][CH3:24])=[CH:7][CH:6]=[CH:5][N:4]2[C:8]=1[CH3:12]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 131847782,6-DiethylbenzaldehydeHCID 218739802,3-Dimethylimidazo[1,2-a]pyridin-8-amine

Product 1

HCID 217173502,3-Dimethyl-8-(2,6-diethylbenzylamino)-imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

8-amino-2,3-dimethyl-imidazo[1,2-a]pyridine (0.33 g, 2.0 mmol) and 2,6-diethylbenzaldehyde (0.36 g, 2.2 mmol) were dissolved in methanol (7 ml). ZnCl2 (0.30 g, 2.2 mmol) and subsequently NaBH3CN (0.14 g, 2.2 mmol) in small portions were added and the mixture was refluxed under argon for 3 hours, cooled and then poured over an aqueous 1M NaOH solution (10 ml). The resultant yellow suspension was extracted with DCM (3×25 ml) and the combined organic solutions were washed with brine, dried over Na2SO4 and then removed. The oily residue (0.4 g) was purified by flash chromatography (DCM-EtOAc 0%-20% EtOAc) to give 0.34 g. Treatment of this oily product with hexane (2 ml) afforded 0.14 g (23%) as off-white crystals.

Workup

  1. temperaturethe mixture was refluxed under argon for 3 hours
  2. temperaturecooled
  3. extractionThe resultant yellow suspension was extracted with DCM (3×25 ml)
  4. washthe combined organic solutions were washed with brine
  5. dry with materialdried over Na2SO4
  6. customremoved
  7. customThe oily residue (0.4 g) was purified by flash chromatography (DCM-EtOAc 0%-20% EtOAc)
  8. customto give 0.34 g

Sources & evidence

ORD record
ord-754303612eb64590bcff75744c3659ab
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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