Sodium hydride → HCID 9861350, compound

HRID 1582698Notes

Reaction equation

HRID 1582698 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:18]=[CH:17][NH:16][N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:21](Cl)(=[O:25])[CH:22]([CH3:24])[CH3:23]>CN(C=O)C>[CH3:23][CH:22]([CH3:24])[C:21]([N:16]1[CH:17]=[CH:18][C:14]([C:11]2[CH:12]=[CH:13][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:9][CH:10]=2)=[N:15]1)=[O:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 62325Isobutyryl chlorideHCID 178420501HCID 178420501, compound

Product 1

HCID 9861350HCID 9861350, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(4-phenoxyphenyl)-1H-pyrazole (123 mg, 0.52 mmol) and NaH (28 mg, 0.70 mmol) in 5 mL of DMF was stirred at room temperature for 30 minutes. Neat isobutyryl chloride (80 μL, 0.75 mmol) was added and the reaction was stirred at room temperature. The reaction was then partitioned between water and EtOAc. The aqueous layer was extracted twice with EtOAc and the pooled organic layers were dried (Na2SO4), filtered and concentrated in vacuo. Column chromatography (5% EtOAc/hexane) gave 127 mg (80%) of the title compound as a white solid, mp 49-51° C. 1H NMR (CDCl3): δ 8.30 (d, J=3.0 Hz, 1H), 7.88 (d, J=8.7 Hz, 2H), 7.39 (t, J=8.0 Hz, 2H), 7.17 (t, J=7.2 Hz, 2H), 7.12-7.08 (m, 4H), 6.75 (d, J=3.0 Hz, 1H), 4.03 (m, 1H), 1.78 (d, J=6.9 Hz, 6H).

Workup

  1. stirringthe reaction was stirred at room temperature
  2. customThe reaction was then partitioned between water and EtOAc
  3. extractionThe aqueous layer was extracted twice with EtOAc
  4. dry with materialthe pooled organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-434608284e8b49469ba187483ccd2a52
Source dataset
uspto-grants-2004_05
Patent number
US06737418B2

Reaction notes

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