Ethyl 1-(4-fluorophenyl)-6-((2-methylpyrimidin-5-yl)ethynyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate → Ethyl 1-(4-fluorophenyl)-6-(2-(2-methylpyrimidin-5-yl)ethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1048887Notes

Reaction equation

HRID 1048887 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([C:18]#[C:19][C:20]4[CH:21]=[N:22][C:23]([CH3:26])=[N:24][CH:25]=4)=[CH:15][CH:16]=3)[C:11](=[O:27])[C:10]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:9]2)=[CH:4][CH:3]=1>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([CH2:18][CH2:19][C:20]4[CH:25]=[N:24][C:23]([CH3:26])=[N:22][CH:21]=4)=[CH:15][CH:16]=3)[C:11](=[O:27])[C:10]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 121447949Ethyl 1-(4-fluorophenyl)-6-((2-methylpyrimidin-5-yl)ethynyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 121447854Ethyl 1-(4-fluorophenyl)-6-(2-(2-methylpyrimidin-5-yl)ethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound P (25 mg, 0.059 mmol, 1.0 eq) was dissolved in methanol (2 mL) and palladium on carbon (1 mg) was added. The reaction was pumped and purged with hydrogen and allowed to stir overnight. The reaction was filtered over Celite® and washed with 5% methanol in DCM. The organics were concentrated and purified using reverse phase chromatography to afford 16 mg (63%) of title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.54 (s, 2H), 8.41 (s, 1H), 8.09 (d, J=2.0 Hz, 1H), 7.74-7.71 (m, 2H), 7.55 (dd, J=8.7, 2.1 Hz, 1H), 7.50 (t, J=8.8 Hz, 2H), 6.89 (d, J=8.7 Hz, 1H), 4.20 (q, J=7.1 Hz, 2H), 3.04 (t, J=8.3 Hz, 2H), 2.89 (t, J=8.3 Hz, 2H), 2.53 (s, 3H), 1.24 (t, J=7.1 Hz, 3H); ES-MS [M+1]+: 432.3.

Workup

  1. custompurged with hydrogen
  2. filtrationThe reaction was filtered over Celite®
  3. washwashed with 5% methanol in DCM
  4. concentrationThe organics were concentrated
  5. custompurified

Sources & evidence

ORD record
ord-6ee6618fcd13414aa3c03fc5186f3a78
Source dataset
uspto-grants-2016_07
Patent number
US09382208B1

Reaction notes

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