Benzoyl Peroxide → methyl 7-(bromomethyl)-8-fluoro-4-(1-methyl-1H-pyrazol-4-yl)quinoline-2-carboxylate

HRID 922806Notes

Reaction equation

[F:1][C:2]1[C:3]([CH3:22])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[C:7]2[C:16]1[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=1.C1C(=O)N([Br:30])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:30][CH2:22][C:3]1[C:2]([F:1])=[C:11]2[C:6]([C:7]([C:16]3[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=3)=[CH:8][C:9]([C:12]([O:14][CH3:15])=[O:13])=[N:10]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

After degassing with N2, a mixture of methyl 8-fluoro-7-methyl-4-(1-methyl-1H-pyrazol-4-yl)quinoline-2-carboxylate (7-17, 169.2 mg, 0.57 mmol), NBS (106 mg, 0.59 mmol) and benzoyl peroxide (13.7 mg, 0.057 mmol) in CCl4 (2.8 ml) was stirred at 80° C. After 5 h, the solvent was removed and the residue was partitioned between EtOAC and sat. NaHCO3. The organic layer was washed with water, dried over Na2SO4 and filtered. Concentration afforded the crude methyl 7-(bromomethyl)-8-fluoro-4-(1-methyl-1H-pyrazol-4-yl)quinoline-2-carboxylate, which was used without further purification (7-18). LRMS m/z (M+H)+ 378.2 found, 378.0 required.

Workup

customAfter degassing with N2
customthe solvent was removed
customthe residue was partitioned between EtOAC and sat. NaHCO3
washThe organic layer was washed with water
dry with materialdried over Na2SO4
filtrationfiltered
concentrationConcentration

Sources & evidence

ORD record: ord-859039d6c34c4952aed537056bbb0458
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278960B2

Reaction notes

Loading…