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Potassium Carbonate → 2,6-Dimethylisoquinolin-1-one

HRID 518296
Notes
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Reaction equation

HRID 518296 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]B(O)O.C([O-])([O-])=O.[K+].[K+]>O.O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][N:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH3:14])[CH:3]=2)[C:8]1=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 231581786-Bromo-2-methyl-1,2-dihydroisoquinolin-1-one

Product 1

HCID 140926042,6-Dimethylisoquinolin-1-oneYield 82.8%

Reagents, catalysts & solvents 3

HCID 962WaterCatalyst
HCID 178418397
HCID 178418397, compound
Catalyst
HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-bromo-2-methylisoquinolin-1-one (200.0 mg, 0.84 mmol), methylboronic acid (251.0 mg, 4.2 mmol), Pd(PPh3)4 (93.0 mg, 0.08 mmol), K2CO3 (232.0 mg, 1.68 mmol) and H2O (2 drops) in dioxane (10.0 mL) was microwaved at 120° C. for 1 h. Purification by silica gel chromatography (PE:EA=5:1) gave the title compound (120.0 mg, 82.8%) as a light yellow solid. LCMS: 174.3 (M+H)+.

Workup

  1. customwas microwaved at 120° C. for 1 h
  2. customPurification by silica gel chromatography (PE:EA=5:1)

Sources & evidence

ORD record
ord-ea6d06431c684feaa1c8ef0114597e06
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09115114B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes