Potassium Carbonate → 3-chloro-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridine

HRID 254416Notes

Reaction equation

Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[F:9][C:10]([F:17])([F:16])[C:11]1[CH:15]=[CH:14][NH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:8][C:7]1[C:2]([N:13]2[CH:14]=[CH:15][C:11]([C:10]([F:17])([F:16])[F:9])=[N:12]2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 117.5 °C

Procedure

To a mixture of 2,3-dichloropyridine (99.0 g, 0.67 mol) and 3-(trifluoromethyl)-pyrazole (83 g, 0.61 mol) in dry N,N-dimethylformamide (300 mL) was added potassium carbonate (166.0 g, 1.2 mol) and the reaction was then heated to 110-125° C. over 48 hours. The reaction was cooled to 100° C. and filtered through Celite® diatomaceous filter aid to remove solids. N,N-Dimethylformamide and excess dichloropyridine were removed by distillation at atmospheric pressure. Distillation of the product at reduced pressure (b.p. 139-141° C., 7 mm) afforded 113.4 g of the desired intermediate as a clear yellow oil.

Workup

temperatureThe reaction was cooled to 100° C.
filtrationfiltered through Celite® diatomaceous filter aid
customto remove solids
customN,N-Dimethylformamide and excess dichloropyridine were removed by distillation at atmospheric pressure
distillationDistillation of the product at reduced pressure (b.p. 139-141° C., 7 mm)

Sources & evidence

ORD record: ord-bc2947a7131b4f6a8bacccd87a8d0c31
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875634B2

Reaction notes

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