Dimethylformamide → HCID 67260752, compound

HRID 2359047Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)=[N:10][N:11]([CH:13]([CH2:15][CH3:16])[CH3:14])[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[CH3:23][N:24](C)C=O>[C-]#N.[Zn+2].[C-]#N>[C:23]([C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)=[N:10][N:11]([CH:13]([CH2:15][CH3:16])[CH3:14])[CH:12]=2)[CH:5]=[CH:4][N:3]=1)#[N:24]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 2-chloro-4-[1-sec-butyl-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (0.28 mmol) in 1 mL of N,N-dimethylformamide was added zinc cyanide (0.14 mmol) and tetrakistriphenylphosphine palladium (O) (0.057 mmol). The resulting mixture was stirred in the microwave for 10 min at 120° C. After cooling to room temperature, the mixture was filtered and purified by preparative HPLC (column: Waters Sunfire C18, eluent:water/methanol/0.1% formic acid) to afford 56.7 mg of 2-cyano-4-[1-sec-butyl-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (55% yield).

Workup

temperatureAfter cooling to room temperature
filtrationthe mixture was filtered
custompurified by preparative HPLC (column: Waters Sunfire C18, eluent:water/methanol/0.1% formic acid)

Sources & evidence

ORD record: ord-4fd152615e9b4cbda3829788603524d4
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685974B2

Reaction notes

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