Potassium Carbonate → HCID 10285978, compound

HRID 2099512Notes

Reaction equation

[NH:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)[CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].F[C:19]1[N:24]=[C:23]([C:25]#[N:26])[CH:22]=[CH:21][CH:20]=1>CN(C=O)C.CCOC(C)=O>[N:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:4]1[CH:5]=[N:1][N:2]([C:19]2[N:24]=[C:23]([C:25]#[N:26])[CH:22]=[CH:21][CH:20]=2)[CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

2-(1H-Pyrazol-4-yl)pyridine (300 mg, 2.0 mmol) was dissolved in DMF (10 mL), potassium carbonate (566 mg, 4 mmol) and 6-fluoropyridine-2-carbonitrile (250 mg, 2 mmol) was added. The reaction was heated at 140° C. for 16 h. The crude mixture was cooled to rt and diluted with EtOAc (300 mL) and washed with H2O (200 mL) and brine (200 mL). The organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexanes:EtOAc (7:3) to afford 6-(4-pyridin-2-yl-1H-pyrazol-1-yl)pyridine-2-carbonitrile. This material was dissolved in methylene chloride (5 mL) and, upon treatment with 1M HCl in diethyl ether (0.6 mL), precipitated as the hydrochloride salt. M.P. 260-261° C. 1H-NMR (CDCl3, 300 MHz) δ 9.67 (s, 1H), 8.83 (s, 1H), 8.79-8.77 (d, J=6 Hz, 1H), 8.47-8.29 (m, 4H), 8.13-8.10 (m, 1H) 7.77-7.73 (t, 1H). MS ESI) 249 (M++H).

Workup

washwashed with H2O (200 mL) and brine (200 mL)
dry with materialThe organic phase was dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel eluting with hexanes:EtOAc (7:3)

Sources & evidence

ORD record: ord-0dfc75360f684ecba5516dbb27d38ce3
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569592B2

Reaction notes

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