Sodium borohydride → N-(3-(4-fluorophenyl)-1-(2-hydroxyethyl)-4-(phenylethynyl)-1H-pyrazol-5-yl)acetamide

HRID 1775576Notes

Reaction equation

HRID 1775576 reaction equation
[C:1]([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][C:19]([F:22])=[CH:18][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:3])[CH3:2].[BH4-].[Na+]>C(O)C.CO>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:7]2[C:6]([C:23]#[C:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[N:9]([CH2:10][CH2:11][OH:12])[N:8]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 70982686ethyl 2-(5-acetamido-3-(4-fluorophenyl)-4-(phenylethynyl)-1H-pyrazol-1-yl)acetate

Product 1

HCID 70983184N-(3-(4-fluorophenyl)-1-(2-hydroxyethyl)-4-(phenylethynyl)-1H-pyrazol-5-yl)acetamideYield 72.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-(5-acetamido-3-(4-fluorophenyl)-4-(phenylethynyl)-1H-pyrazol-1-yl)acetate (1 g, 2.5 mmol) in ethanol (40 mL) and methanol (10 ml) was added sodium borohydride (466 mg, 12.3 mmol and the reaction stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo and the residue was dissolved in CH2Cl2 and washed with a dilute NH4Cl solution. The aqueous was extracted with CH2Cl2 and the combined organic extracts were dried over MgSO4, filtered and evaporated. The crude product was suspended in CH2Cl2 (20 ml), heated to reflux, allowed to cool and the product was filtered and dried in vacuo to give N-(3-(4-fluorophenyl)-1-(2-hydroxyethyl)-4-(phenylethynyl)-1H-pyrazol-5-yl)acetamide as a white solid (659 mg), which was used as such in the subsequent step.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washwashed with a dilute NH4Cl solution
  4. extractionThe aqueous was extracted with CH2Cl2
  5. dry with materialthe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. temperatureheated
  9. temperatureto reflux
  10. temperatureto cool
  11. filtrationthe product was filtered
  12. customdried in vacuo

Sources & evidence

ORD record
ord-c5d7d8f3f925489db033689728666ec7
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

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