Triethylamine → 4-(1-(4-(trifluoromethoxy)phenyl)-1H-pyrazol-3-yl)benzoyl azide

HRID 59869Notes

Reaction equation

HRID 59869 reaction equation
[F:1][C:2]([F:25])([F:24])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[CH:13][C:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.C1(P([N:47]=[N+:48]=[N-:49])(C2C=CC=CC=2)=O)C=CC=CC=1>C(O)(C)C>[F:1][C:2]([F:25])([F:24])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[CH:13][C:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([N:47]=[N+:48]=[N-:49])=[O:20])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 581567244-(1-(4-(Trifluoromethoxy)phenyl)-1H-pyrazol-3-yl)benzoic acid

Product 1

HCID 866758054-(1-(4-(trifluoromethoxy)phenyl)-1H-pyrazol-3-yl)benzoyl azideYield 30.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 4-(1-(4-(trifluoromethoxy)phenyl)-1H-pyrazol-3-yl)benzoic acid (0.58 g, 1.67 mmol) in isopropanol (10.7 mL) was added triethylamine (0.30 mL, 2.17 mmol) and diphenylphosphoryl azide (0.47 mL, 2.17 mmol) and the reaction was stirred at room temperature for 16 hours. The orange precipitate that had formed was filtered through a fritted glass funnel, rinsed with isopropanol, and dried in a vacuum oven to provide 4-(1-(4-(trifluoromethoxy)phenyl)-1H-pyrazol-3-yl)benzoyl azide as an orange solid (188 mg, 30%): 1H NMR (400 MHz, DMSO-d6) δ 8.69 (d, J=2.6 Hz, 1H), 8.17-8.11 (m, 2H), 8.09-8.04 (m, 4H), 7.57 (d, J=8.4 Hz, 2H), 7.24 (d, J=2.6 Hz, 1H); 19F NMR (376 MHz, DMSO-d6) δ −56.97; ESIMS m/z 374 ([M+H]+).

Workup

  1. customThe orange precipitate that had formed
  2. filtrationwas filtered through a fritted glass funnel
  3. washrinsed with isopropanol
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-5920dbb9cdca47c7be274f71792d3654
Source dataset
uspto-grants-2016_09
Patent number
US09440964B2

Reaction notes

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