Bromine → 4-Bromo-2-methyl-6-(1-methylpyrazol-4-yl)isoquinolin-1-one

HRID 575548Notes

Reaction equation

HRID 575548 reaction equation
[Br:1]Br.[CH3:3][N:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:14]3[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=3)[CH:10]=2)[C:5]1=[O:20]>CC(O)=O>[Br:1][C:12]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:14]3[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=3)[CH:10]=2)[C:5](=[O:20])[N:4]([CH3:3])[CH:13]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 1180214282-Methyl-6-(1-methylpyrazol-4-yl)isoquinolin-1-one

Product 1

HCID 1180215864-Bromo-2-methyl-6-(1-methylpyrazol-4-yl)isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Bromine (1.8 g, 11.25 mmol) in HOAc (6 mL) was added to the title compound of 2-methyl-6-(1-methylpyrazol-4-yl)isoquinolin-1-one (3 g, 12.5 mmol) in HOAc (24 mL) at 0° C. The mixture was stirred at 30° C. for 15 min, quenched with H2O (100 mL), and the resulting yellow solid was collected by filtration to give the title compound (2.04 g, 56%). 1H NMR (CDCl3, 400 MHz) δ 8.42 (d, J=8.4 Hz, 1H), 7.87 (d, J=28.8 Hz, 2H), 7.82 (d, J=15.6 Hz, 2H), 7.65 (d, J=8 Hz, 2H), 7.38 (s, 1H), 4.00 (s, 3H), 3.61 (s, 3H). LCMS: 318.0 (M+H)+

Sources & evidence

ORD record
ord-33cca8c8143e4c069ba31f8df19a9296
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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