Sodium Bicarbonate → HCID 76849567, compound

HRID 1802770Notes

Reaction equation

HRID 1802770 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[C:10]=1[CH:11]=[CH:12][O:13]CC[Si](C)(C)C.C(=O)(O)[O-].[Na+]>C(#N)C.O>[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[C:10]=1[CH2:11][CH:12]=[O:13]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 67159028HCID 67159028, compound

Product 1

HCID 76849567HCID 76849567, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-methyl-3-[2-(2-trimethylsilanyl-ethoxy)-vinyl]-imidazo[1,2-a]pyridine (1.8 g, 6.56 mmol) in a mixture of acetonitrile and water (1:1 by volume, 16 mL) in a 100 mL plastic bottle was added HF (8 mL, 48% solution in water). The reaction mixture was stirred at room temperature for 96 h and solid sodium bicarbonate was added in batches until the mixture reached pH 6. The mixture was washed twice with ether, basified to pH 8 with solid sodium hydroxide, and extracted three times with dichloromethane. The combined dichloromethane extracts were dried over magnesium sulfate and concentrated in vacuo to give (2-methyl-imidazo[1,2-a]pyridin-3-yl)-acetaldehyde (922 mg) as a deep brown semi-solid that was used directly in the next step without further purification.

Workup

  1. washThe mixture was washed twice with ether
  2. extractionextracted three times with dichloromethane
  3. dry with materialThe combined dichloromethane extracts were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-59d5483097fc4b368278fb19d36aaf37
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

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