Sodium Bicarbonate → HCID 115938202, compound

HRID 1526282Notes

Reaction equation

HRID 1526282 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:13]=1[CH2:14][NH2:15].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O1CCCC1.C(O)(=O)C>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][NH:15][CH2:14][C:13]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:12]=2[O:11][CH3:10])[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5972502,4-DimethoxybenzylamineHCID 27570096-Bromopyridine-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 115938202HCID 115938202, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-Bromopicoline aldehyde (0.520 g) and 2,4-dimethoxybenzylamine (0.504 mL) were dissolved in tetrahydrofuran (25 mL), acetic acid (0.176 mL) was added thereto, and the mixture was stirred at room temperature for 1 hr. Sodium triacetoxyborohydride (889 mg) was added thereto, and the mixture was stirred in a second straight night at room temperature. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, 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 (hexane/ethyl acetate) to give the title compound (930 mg).

Workup

  1. stirringthe mixture was stirred in a second straight night at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-61af74f5466243e587c57ba9718ff009
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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