Potassium Carbonate → 5-iodo-2-(4-phenyl-1H-pyrazol-1-yl)pyridine

HRID 537435Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1.[C:9]1([C:15]2[CH:16]=[N:17][NH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[I:8][C:5]1[CH:6]=[CH:7][C:2]([N:17]2[CH:16]=[C:15]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:19]=[N:18]2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 2-fluoro-5-iodopyridine (368.3 mg, 1.652 mmol), 4-phenyl-1H-pyrazole (238.2 mg, 1.652 mmol), and potassium carbonate (457 mg, 3.30 mmol) in N,N-dimethylformamide (3.30 mL) was heated to 85° C. for 21 hours. The reaction was then concentrated and the crude residue diluted with water and ethyl acetate. The layers were separated and the aqueous was extracted two more times with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered, and concentrated to give 5-iodo-2-(4-phenyl-1H-pyrazol-1-yl)pyridine (537.2 mg, 94%) as a white solid. 1H NMR (400 MHz, CDCl3, δ): 8.76 (s, 1H), 8.61 (d, J=1.8 Hz, 1H), 8.09 (dd, J=8.7, 2.2 Hz, 1H), 8.01 (s, 1H), 7.82 (d, J=8.6 Hz, 1H), 7.55-7.61 (m, 2H), 7.36-7.43 (m, 2H), 7.25-7.31 (m, 1H). MS (M+1): 348.0.

Workup

concentrationThe reaction was then concentrated
additionthe crude residue diluted with water and ethyl acetate
customThe layers were separated
extractionthe aqueous was extracted two more times with ethyl acetate
dry with materialThe combined organics were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-1da442f6521f4130b827e6b41ceb748a
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859591B2

Reaction notes

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