Sodium Hydroxide → 8-(4-Methoxy-2,6-dimethylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine

HRID 1006663Notes

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.[CH3:13][O:14][C:15]1[CH:22]=[C:21]([CH3:23])[C:18]([CH:19]=O)=[C:17]([CH3:24])[CH:16]=1.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH3:13][O:14][C:15]1[CH:22]=[C:21]([CH3:23])[C:18]([CH2:19][NH:1][C:2]2[C:3]3[N:4]([C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=3)[CH:5]=[CH:6][CH:7]=2)=[C:17]([CH3:24])[CH:16]=1

Participants

Conditions

Temperature: 2.5 °C

Procedure

8-amino-2,3-dimethylimidazo[1,2-a]pyridine (0.5 g, 3.1 mmol), 4-methoxy-2.6-dimethylbenzaldehyd (0.51 g, 3.11 mmol) were dissolved in methanol (10 ml) whereupon zinc chloride (0.51 g, 3.82 mmol) dissolved in methanol (5 ml) was added. Sodium cyanoborohydride was added in portions and the mixture was refluxed for 3 h under under nitrogen. The mixture was stirred at 0-5° C. and 1 M sodium hydroxide (20 ml) was added. After extraction with 2×50 ml of methylene chloride the combined organic layer was washed with water and dried over sodium sulfate. The solvent was removed under reduced pressure. The residue was chromatographed on silica (dichloromethane: ethyl acetate, 1:1) yielding 0.58 g 60% of the title compound.

Workup

additionwas added
temperaturethe mixture was refluxed for 3 h under under nitrogen
extractionAfter extraction with 2×50 ml of methylene chloride the combined organic layer
washwas washed with water
dry with materialdried over sodium sulfate
customThe solvent was removed under reduced pressure
customThe residue was chromatographed on silica (dichloromethane: ethyl acetate, 1:1)

Sources & evidence

ORD record: ord-2ae01a938c03425085f6257ded584db3
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06790960B2

Reaction notes

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