Water → 2-[1-(3-chlorophenyl)-1H-pyrazol-3-yl]pyridine

HRID 2099505Notes

Reaction equation

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

Participants

Conditions

Temperature: 145 °C

Procedure

2-(1H-Pyrazol-3-yl)pyridine (435 mg, 3 mmol), 3-fluoro-1-chlorobenzene (0.32 mL, 3 mmol) and K2CO3 (830 mg, 6 mmol) were dissolved in DMF (10 mL) under Ar (g) and heated at 145° C. for 18 h. After cooling to ambient temperature, H2O (40 mL) and EtOAc (40 mL) were added and the reaction mixture shaken, the EtOAc layer was separated and the aqueous layer shaken with EtOAc (2×30 mL). The combined organic layers were washed with brine (3×40 mL), dried over Na2SO4 and concentrated onto silica gel. The crude material was purified by liquid chromatography on silica gel, eluting with EtOAc:hexane (1:1) to afford 2-[1-(3-chlorophenyl)-1H-pyrazol-3-yl]pyridine as as solid. 1H NMR (CD3Cl, 300 MHz) δ 8.68-8.69 (1H, m), 8.13-8.16 (1H, m), 8.01 (1H, m), 7.88 (11H, m), 7.79 (1H, ddd), 7.66-7.68 (1H, m), 7.42 (1H, dd), 7.26-7.31 (2H, m), 7.16 (1H, d). MS (ESI) 256 (M+H)+

Workup

temperatureAfter cooling to ambient temperature
customthe EtOAc layer was separated
stirringthe aqueous layer shaken with EtOAc (2×30 mL)
washThe combined organic layers were washed with brine (3×40 mL)
dry with materialdried over Na2SO4
concentrationconcentrated onto silica gel
customThe crude material was purified by liquid chromatography on silica gel
washeluting with EtOAc:hexane (1:1)

Sources & evidence

ORD record: ord-674d8f7f59364e6696a3ecbb50ab5572
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569592B2

Reaction notes

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