Sodium Bicarbonate → HCID 83520412, compound

HRID 869572Notes

Reaction equation

HRID 869572 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[N:5][CH:6]=[CH:7][CH:8]=1.Br[CH2:11][C:12](=O)[CH:13]([CH3:15])[CH3:14].C(=O)([O-])O.[Na+]>C(O)C>[CH:13]([C:12]1[N:9]=[C:4]2[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][N:5]2[CH:11]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 99203842-Amino-3-methoxypyridineHCID 108990371-Bromo-3-methylbutan-2-one

Product 1

HCID 83520412HCID 83520412, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

[step 1] Commercially available 3-methoxypyridin-2-amine (1.0 g, 8.06 mmol) was dissolved in ethanol (8.1 mL), 1-bromo-3-methylbutan-2-one (Organic Syntheses, 1976, vol. 55, p 24; 1.46 g, 8.86 mmol) was added, and the mixture was stirred at 110° C. for 13 hr. To the mixture was added saturated aqueous sodium hydrogen carbonate, and the mixture was extracted 3 times with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-30/70 v/v) to give 2-isopropyl-8-methoxyimidazo[1,2-a]pyridine (746 mg, 49%).

Workup

  1. addition1.46 g, 8.86 mmol) was added
  2. extractionthe mixture was extracted 3 times with chloroform
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-30/70 v/v)

Sources & evidence

ORD record
ord-5a65e5d9a8f04fe5ba48dd6d6d260eb5
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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