Sodium hydride → HCID 9861350, compound

HRID 2227720Notes

Reaction equation

HRID 2227720 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): δ8.30 (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-8b10110541a4466890c8528222cfd2c7
Source dataset
uspto-grants-2002_07
Patent number
US06414011B1

Reaction notes

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