Sodium borohydride → HCID 89852607, compound

HRID 1746895Notes

Reaction equation

HRID 1746895 reaction equation
[CH:1]([C:3]1[CH:7]=[CH:6][N:5]([C:8]2[N:18]=[CH:17][CH:16]=[CH:15][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:4]=1)=[O:2].[BH4-].[Na+]>C(O)C>[OH:2][CH2:1][C:3]1[CH:7]=[CH:6][N:5]([C:8]2[N:18]=[CH:17][CH:16]=[CH:15][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 89851914HCID 89851914, compound

Product 1

HCID 89852607HCID 89852607, compoundYield 297.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

To ethyl 2-(3-formyl-1H-pyrazol-1-yl)nicotinate (6 g, 9.79 mmol) in ethanol (100 mL) at 10° C. NaBH4 (0.741 g, 19.57 mmol) was added and stirred at 25° C. for 1 hr. For work up the mixture was poured into 200 mL of ice water, extracted twice with ethyl acetate, the combined organic layers subsequently washed with water and brine, dried (MgSO4), filtered and concentrated to give 7.2 g of a yellow oil. Purification by chromatography over silica gel (eluent CH2Cl2+0-10% methanol) gave 2.36 g of the corresponding title compound as clear oil; ESI-MS [M+H]+: 248.1.

Workup

  1. customat 10° C
  2. extractionextracted twice with ethyl acetate
  3. washthe combined organic layers subsequently washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b1e88573bccc49e2abee25b50b7f9851
Source dataset
uspto-grants-2015_10
Patent number
US09150545B2

Reaction notes

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