Potassium Cyanide → Ethyl 1-[4-(4-cyano-1H-pyrazol-1-yl)benzyl]-5-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1969440Notes

Reaction equation

[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:30])[C:5]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:6][N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH:23]=[C:22](I)[CH:21]=[N:20]2)=[CH:15][CH:14]=1.[C-:31]#[N:32].[K+].C([Sn](Cl)(CCCC)CCCC)CCC>C(#N)C.C(P([Pd]P(C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:31]([C:22]1[CH:21]=[N:20][N:19]([C:16]2[CH:17]=[CH:18][C:13]([CH2:12][N:7]3[C:8]4[C:3](=[C:2]([F:1])[CH:11]=[CH:10][CH:9]=4)[C:4](=[O:30])[C:5]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:6]3)=[CH:14][CH:15]=2)[CH:23]=1)#[N:32]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of ethyl 5-fluoro-1-[4-(4-iodo-1H-pyrazol-1-yl)benzyl]-4-oxo-1,4-dihydroquinoline-3-carboxylate (0.100 g, 0.193 mmol), potassium cyanide (0.038 g, 0.52 mmol), and tributyltin chloride (0.68 mg, 1.9 μmol) in 2 mL of acetonitrile under nitrogen was added bis(tri-tert-butylphosphoranyl)palladium (10 mol %). The reaction mixture was stirred at 120° C. for 48 hours, cooled to room temperature, and purified via reverse phase HPLC to provide the title compound which gave a proton NMR spectrum consistent with theory. This compound could be further hydrolyzed to the corresponding carboxylic acid, as described in Example 1.

Workup

temperaturecooled to room temperature
custompurified via reverse phase HPLC

Sources & evidence

ORD record: ord-e8919e8c40564f5da343dc0d11f4a161
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426598B2

Reaction notes

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