Pyrazole → HCID 9992423, compound

HRID 2099515Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N:10]2[CH:14]=[C:13](I)[CH:12]=[N:11]2)[CH:9]=1)[C:5]#[N:6].[NH:16]1[CH:20]=[CH:19][CH:18]=[N:17]1.C(=O)([O-])[O-].[K+].[K+]>[Cu]I>[N:16]1([C:13]2[CH:12]=[N:11][N:10]([C:8]3[CH:7]=[C:4]([CH:3]=[C:2]([F:1])[CH:9]=3)[C:5]#[N:6])[CH:14]=2)[CH:20]=[CH:19][CH:18]=[N:17]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a sealed tube containing dry, deoxygenated dioxane (1 mL) was added 3-fluoro-5-(4-iodo-1H-pyrazol-1-yl)benzonitrile (313 mg, 1.0 mmol), pyrazole (88 mg, 1.3 mmol), trans-diaminocyclohexane (24 μL, 0.2 mmol), potassium carbonate (304 mg, 2.2 mmol), and CuI (4 mg, 0.02 mmol). The reaction was capped and heated with stirring for 48 hr at 100° C. The resulting mixture was partitioned with EtOAc (10 mL) and H2O (10 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo on to a plug of silica gel, which was loaded on to a prepacked column and purified via automated flash chromatography utilizing a 5-35% EtOAc/Hexanes gradient to afford 3-(1′H-1,4′-bipyrazol-1′-yl)-5-fluorobenzonitrile as a white solid. 1H NMR (CDCl3, 500 MHz) δ 8.48 (s, 1H), 8.04 (s, 1H), 7.96 (m, 1H), 7.85-7.88 (m, 2H), 7.71 (d, 1H), 7.36 (m, 1H), 6.50 (m, 1H). MS (ESI) 254.15 (M++H).

Workup

additionTo a sealed tube containing
customdry
customdeoxygenated dioxane (1 mL)
customThe reaction was capped
temperatureheated
customThe resulting mixture was partitioned with EtOAc (10 mL) and H2O (10 mL)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo on to a plug of silica gel, which
custompurified via automated flash chromatography

Sources & evidence

ORD record: ord-837f5997bc614df09e0273372166b746
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569592B2

Reaction notes

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