Triphenylphosphine → Ethyl 1-(4-fluorophenyl)-6-(((2-methylpyrimidin-5-yl)oxy)methyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1048881Notes

Reaction equation

HRID 1048881 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]([CH2:18][OH:19])=[CH:15][CH:16]=3)[C:11](=[O:20])[C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:9]2)=[CH:4][CH:3]=1.O[C:27]1[CH:28]=[N:29][C:30]([CH3:33])=[N:31][CH:32]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([CH2:18][O:19][C:27]4[CH:28]=[N:29][C:30]([CH3:33])=[N:31][CH:32]=4)=[CH:15][CH:16]=3)[C:11](=[O:20])[C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5358572-Methylpyrimidin-5-olHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 121447982Ethyl 1-(4-fluorophenyl)-6-(hydroxymethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 121447956Ethyl 1-(4-fluorophenyl)-6-(((2-methylpyrimidin-5-yl)oxy)methyl)-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound J (16 mg, 0.047 mmol) and 5-hydroxy-2-methylpyrimidine (6.2 mg, 0.056 mmol) in THF (1 mL) cooled to 0° C. was added triphenylphosphine (27.1 mg, 0.10 mmol) and di-tert-butylazodicarboxylate (17.3 mg, 0.075 mmol). The reaction was concentrated to dryness after 16 hours of stirring. Purification by reverse phase HPLC afforded 20 mg (98%) of the title compound. ES-MS [M+1]+: 434.3.

Workup

  1. concentrationThe reaction was concentrated to dryness after 16 hours
  2. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-cb538f18cdf14126ba3bcd8e05d73b03
Source dataset
uspto-grants-2016_07
Patent number
US09382208B1

Reaction notes

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