Sodium borohydride → HCID 89995678, compound

HRID 523102Notes

Reaction equation

HRID 523102 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=[O:8])=[C:5]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:4]=[N:3]1.[BH4-].[Na+]>CO>[CH3:1][N:2]1[C:6]([CH2:7][OH:8])=[C:5]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 754868652-Methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-3-carbaldehyde

Product 1

HCID 89995678HCID 89995678, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-5-carbaldehyde (Preparation 142, 80 mg, 0.339 mmol) in MeOH (4 mL) at room temperature was added NaBH4 (25.6 mg, 0.678 mmol). The resulting solution was stirred at room temperature for 2 hours before concentrating in vacuo. EtOAc (10 mL) and water (0.5 mL) were added to the residue and the mixture was dried over Na2SO4 and concentrated in vacuo to afford the title compound as a white solid (26 mg, 32%).

Workup

  1. concentrationbefore concentrating in vacuo
  2. additionEtOAc (10 mL) and water (0.5 mL) were added to the residue
  3. dry with materialthe mixture was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be9f1b8e96a0412e8bf2186f2034f872
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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