Bromine → 4-Bromo-2-methyl-6-pyridin-2-ylisoquinolin-1-one

HRID 518308Notes

Reaction equation

HRID 518308 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:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[CH:10]=2)[C:5]1=[O:20]>C(O)(=O)C>[Br:1][C:12]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[CH:10]=2)[C:5](=[O:20])[N:4]([CH3:3])[CH:13]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 1180222082-Methyl-6-pyridin-2-ylisoquinolin-1-one

Product 1

HCID 1180220374-Bromo-2-methyl-6-pyridin-2-ylisoquinolin-1-oneYield 47.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

At 0° C., bromine (78 mg, 0.49 mmol) in acetic acid (0.3 mL) was added dropwise to 2-methyl-6-pyridin-2-ylisoquinolin-1-one (115 mg, 0.49 mmol) in acetic acid (20 mL). The mixture was stirred at room temperature for 20 min. Extractive work up with CH2Cl2 and purification by silica gel chromatography (PE:EA=5:1-1:1) gave the title compound (73.0 mg, 47.7%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.79 (d, J=4.4 Hz, 1H), 8.55 (d, J=8.4 Hz, 1H), 8.44 (s, 1H), 8.19 (d, J=8.8 Hz, 1H), 7.90 (d, J=8.0 Hz, 1H), 7.85 (t, J=7.2 Hz, 1H), 7.42 (s, 1H), 7.36-7.34 (m, 1H), 3.64 (s, 3H). LCMS: 314.9 (M+H)+

Workup

  1. customExtractive work up with CH2Cl2 and purification by silica gel chromatography (PE:EA=5:1-1:1)

Sources & evidence

ORD record
ord-e6ebfbc1714a407283ad79c02393b3ae
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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