Vertellus → HCID 67168013, compound

HRID 1517582Notes

Reaction equation

HRID 1517582 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:19])=[N:8][N:9]([C:11]2[C:16]([CH:17]=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:10]=1)=[O:5])[CH3:2].[B-].[Na+]>CO.C(OCC)(=O)C>[OH:18][CH2:17][C:16]1[C:11]([N:9]2[CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:7]([CH3:19])=[N:8]2)=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 22959485VertellusHCID 58268583HCID 58268583, compound

Product 1

HCID 67168013HCID 67168013, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(3-formyl-pyridin-2-yl)-3-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (1 g, 3.9 mmol) in methanol (25 mL), sodium borohydrate (220.2 mg, 5.8 mmol) is added. The mixture is stirred at room temperature for 2 hr. The solvent is eliminated and the crude is dissolved in ethyl acetate and washed with saturated aqueous solution of ammonium chloride. The organic layer is separated, dried over sodium sulfate, filtered and the solvent evaporated under reduced pressure to give 1 g of ethyl 1-[3-(hydroxymethyl)-2-pyridyl]-3-methyl-pyrazole-4-carboxylate. MS (m/z): 262 (M+1)

Workup

  1. washwashed with saturated aqueous solution of ammonium chloride
  2. customThe organic layer is separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-e92229463842406c9aee9522701dcf7c
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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