Sodium borohydride → HCID 117942228, compound

HRID 1499109Notes

Reaction equation

HRID 1499109 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([N:11]2[CH:15]=[CH:14][C:13]([CH3:16])=[N:12]2)[CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[C:4]([N:11]2[CH:15]=[CH:14][C:13]([CH3:16])=[N:12]2)[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 117941925HCID 117941925, compound

Product 1

HCID 117942228HCID 117942228, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

1-[4-Chloro-2-(3-methyl-pyrazol-1-yl)-phenyl]-ethanone (400 mg, 1.70 mmol) from Step 1 was dissolved in MeOH (10 mL) and cooled to 0° C. NaBH4 (129 mg, 3.41 mmol) was added portionwise, then the reaction was warmed to RT, stirred for 30 min, then quenched with acetone. The MeOH was removed in vacuo then the residue was partitioned between water and EtOAc and extracted several times. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by normal phase silica gel column chromatography (CH2Cl2/MeOH/NH4OH) provided the title compound.

Workup

  1. temperaturethe reaction was warmed to RT
  2. customquenched with acetone
  3. customThe MeOH was removed in vacuo
  4. customthe residue was partitioned between water and EtOAc
  5. extractionextracted several times
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by normal phase silica gel column chromatography (CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-fdf7623f621e4e27aa748903463e5dcb
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

Loading…