tert-Butanol → 1-(3,4-Dichlorophenyl)-5-pyridin-3-yl-1H-pyrazole-3-carbonyl azide

HRID 480101Notes

Reaction equation

Cl.C[O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:8]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[N:7]=1)=O.C(O)(C)(C)C.C1(P([N:44]=[N+:45]=[N-:46])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CN(C=O)C>[Cl:24][C:19]1[CH:18]=[C:17]([N:8]2[C:9]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)=[CH:10][C:6]([C:4]([N:44]=[N+:45]=[N-:46])=[O:3])=[N:7]2)[CH:22]=[CH:21][C:20]=1[Cl:23]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3 (100 mg, 0.27 mmol) and t-butyl alcohol (28.4 μL, 0.30 mmol) in DMF (5 mL, anhydrous) was cooled to 0° C. Diphenylphosphoryl azide (64 μL, 0.30 mmol) was added to the solution. Triethylamine (103 μL, 0.60 mmol) was then added over 10 min. The solution was stirred 1 h at 0° C. and allowed to warm to room temperature and stir 16 h. The reaction was quenched with H2O and extracted with EtOAc. The combined organic layers were washed with H2O, dried (brine and MgSO4), filtered, and concentrated in vacuo. The resulting oil was purified by flash chromatography by eluting with hexane-EtOAc (1:1). Collected 4 (86 mg, 90%) as a yellow crystalline solid.

Workup

temperatureto warm to room temperature
stirringstir 16 h
customThe reaction was quenched with H2O
extractionextracted with EtOAc
washThe combined organic layers were washed with H2O
dry with materialdried (brine and MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting oil was purified by flash chromatography
washby eluting with hexane-EtOAc (1:1)
customCollected 4 (86 mg, 90%) as a yellow crystalline solid

Sources & evidence

ORD record: ord-05d67c7600204cb099e9fda02423b347
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06649638B1

Reaction notes

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