Sodium Bicarbonate → 2-Methyl-6-(6-methylpyridin-3-yl)isoquinolin-1-one

HRID 518293Notes

Reaction equation

HRID 518293 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH3:13])[CH:6]=[CH:5]2.[CH3:14][C:15]1[N:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C([O-])(O)=O.[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:13][N:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:18]3[CH:19]=[N:20][C:15]([CH3:14])=[CH:16][CH:17]=3)[CH:3]=2)[C:8]1=[O:12]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 27630812-Methylpyridine-5-boronic acidHCID 231581786-Bromo-2-methyl-1,2-dihydroisoquinolin-1-one

Product 1

HCID 1180223352-Methyl-6-(6-methylpyridin-3-yl)isoquinolin-1-oneYield 199.8%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-bromo-2-methylisoquinolin-1-one (160 mg, 0.67 mmol), (6-methylpyridin-3-yl)boronic acid (166 mg, 0.32 mmol), Pd(dppf)Cl2 (60 mg, 0.08 mmol) and saturated aqueous NaHCO3 (0.6 mL) in dioxane (6.5 mL) was microwaved at 110° C. for 1.5 h. Purification using silica gel chromatography (PE:EA=3:1 to 2:3) gave the title compound (160 mg, 95.2%) as a yellow solid. LCMS: 251.2 (M+H)+

Workup

  1. customwas microwaved at 110° C. for 1.5 h
  2. customPurification

Sources & evidence

ORD record
ord-79bf698cfee64b058c9f3bf8252bfbcb
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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