Trichloroacetyl chloride → 1-(2-Cyanophenyl)-5-furyl-3-trifluoromethylpyrazole

HRID 1266331Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=2[C:13]([NH2:15])=O)[N:9]=[C:8]([C:20]([F:23])([F:22])[F:21])[CH:7]=1.C(N(CC)CC)C.ClC(Cl)(Cl)C(Cl)=O>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=2[C:13]#[N:15])[N:9]=[C:8]([C:20]([F:22])([F:21])[F:23])[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-[5-(2-Furyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzamide (6.73 g, 21 mmol) and triethylamine (5.8 mL, 42 mmol) were combined in dry CH2Cl2 (55 mL) under argon and cooled to 0° C. Trichloroacetyl chloride (2.7 mL, 24 mmol) in CH2Cl2 (15 mL) was added dropwise over 30 min. The resulting solution was stirred at 0° C. for 20 min, then at room temperature for 65 min. The reaction was quenched with a small amount of water, then partitioned between 1M HCl and CH2Cl2. The organic layer was removed and extracted with sat. NaHCO3, then dried over Na2SO4, filtered, and evaporated to yield crude product (6.66 g). The crude product was chromatographed on silica gel (30-40% EtOAc/hexanes) to yield a yellow solid (6.51 g, >100%). 1H NMR (CDCl3) δ7.79 (m, 2H), 7.64 (m, 2H), 7.39 (d, 1H, J=1.8), 6.96 (s, 1H), 6.37 (m, 1H), 6.04 (d, 1H, J=3.7).

Workup

waitat room temperature for 65 min
customThe reaction was quenched with a small amount of water
custompartitioned between 1M HCl and CH2Cl2
customThe organic layer was removed
extractionextracted with sat. NaHCO3
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated
customto yield crude product (6.66 g)
customThe crude product was chromatographed on silica gel (30-40% EtOAc/hexanes)

Sources & evidence

ORD record: ord-d8bb793a4b8542f980a532280582be56
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548525B2

Reaction notes

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