Sodium Bicarbonate → HCID 67454392, compound

HRID 2389294Notes

Reaction equation

HRID 2389294 reaction equation
[C:1]([C:5]1[N:6]([CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[CH:7]=[C:8]([C:10]2[CH:15]=[N:14][CH:13]=[C:12](Cl)[N:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:24]1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:29]=CC=C[CH:25]=1.[C:70]([O-:73])(=[O:72])C.[K+].C(=O)([O-])O.[Na+]>CN(C=O)C.C(O)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:25]([O:73][C:70]([C:10]1([C:8]2[N:9]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[N:6]([CH2:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH:7]=2)[CH:15]=[N:14][CH:13]=[CH:12][NH:11]1)=[O:72])[CH2:24][CH3:29]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 517044Potassium AcetateHCID 634876Binap, (A+-)-HCID 86642483HCID 86642483, compound

Product 1

HCID 67454392HCID 67454392, compoundYield 843.8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 86598119Dimethylformamide n-propanolSolvent

Conditions

Temperature
80 °C

Procedure

Compound 136 (427 mg, 1.28 mmol) obtained in Example 136 was dissolved in DMF-n-propanol (1/3) (12 mL), and palladium acetate (28.6 mg, 0.128), 2,2′-bis(diphenylphosphino)-1,1′-binaphtyl (79.4 mg, 0.128 mmol), and potassium acetate (151 mg, 1.54 mmol) were added thereto, and the mixture was stirred at 80° C. for 3.5 hours under a carbon monoxide atmosphere. To the mixture, an aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give 2-[2-tert-butyl-1-(tetrahydropyran-4-ylmethyl)-1H-imidazol-4-yl]pyrazine-2-carboxylic acid n-propyl ester (419 mg, 1.08 mmol, yield: 85%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a8ea3e00b0ae4711ad23a288daa44237
Source dataset
uspto-grants-2012_09
Patent number
US08273738B2

Reaction notes

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