Dimethylformamide → HCID 67261259, compound

HRID 2359048Notes

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.[CH:23]([NH2:26])([CH3:25])[CH3:24].CN(C)[CH:29]=[O:30]>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[CH:13]([N:11]1[CH:12]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:29]([NH:26][CH:23]([CH3:25])[CH3:24])=[O:30])[CH:7]=2)[C:9]([C:17]2[S:18][C:19]([Cl:22])=[CH:20][CH:21]=2)=[N:10]1)([CH2:15][CH3:16])[CH3:14]

Participants

Conditions

Temperature: 80 °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 2 mL of N,N-dimethylformamide was added molybdenum hexacarbonyl (0.28 mmol), tetrakistriphenylphosphine palladium (0) (0.028 mmol), isopropylamine (0.85 mmol), and 1,8-diazabicyclo(5-4-0)undece-7-ene (0.85 mmol). The mixture was stirred at 80° C. overnight. The solvent was then evaporated and the residue was purified by chromatography on silica gel (hepthane:ethyl acetate 5:1 to 2:1) to afford 30 mg of 4-[1-sec-butyl-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]-N-isopropylpyridine-2-carboxamide (26% yield).

Workup

customThe solvent was then evaporated
customthe residue was purified by chromatography on silica gel (hepthane:ethyl acetate 5:1 to 2:1)

Sources & evidence

ORD record: ord-de14c57c52ac466685c2e231b1fd2d5b
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685974B2

Reaction notes

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