Sodium Hydroxide → HCID 70983357, compound

HRID 1525459Notes

Reaction equation

HRID 1525459 reaction equation
C([NH:4][C:5]1[N:9]([CH2:10][C:11](OCC)=[O:12])[N:8]=[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:6]=1[C:23]#[C:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=O)C.[BH4-].[Na+].[OH-].[Na+]>C(O)C>[NH2:4][C:5]1[N:9]([CH2:10][CH2:11][OH:12])[N:8]=[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:6]=1[C:23]#[C:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydride2×HCID 70982975HCID 70982975, compound

Product 1

HCID 70983357HCID 70983357, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(5-acetamido-3-(3-fluorophenyl)-4-(phenylethynyl)-1H-pyrazol-1-yl)acetate (3.25 g, 8.02 mmol) in ethanol (90 mL) was added sodium borohydride (610 mg, 16.04 mmol) and the reaction stirred at room temperature for 36 h. Additional sodium borohydride was added (305 mg, 8.02 mmol) and the reaction stirred at room temperature for 3611.25% NaOH (0.9 mL) was added and the reaction mixture was stirred at 80° C. for 3.5 h. The reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was washed with ethyl acetate twice and the organic phases combined, dried over MgSO4, filtered and evaporated. The crude material was suspended in diethylether (30 mL) and the product was filtered and dried in vacuo to give 2-(5-amino-3-(3-fluorophenyl)-4-(phenylethynyl)-1H-pyrazol-1-yl)ethanol as a white solid (2.2 g), which was used as such in the subsequent step.

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred at 80° C. for 3.5 h
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. washThe aqueous phase was washed with ethyl acetate twice
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. filtrationthe product was filtered
  9. customdried in vacuo

Sources & evidence

ORD record
ord-9ac415289fb5496a8c84e5ef1062eb67
Source dataset
uspto-grants-2015_07
Patent number
US09079909B2

Reaction notes

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