CON(C)[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[CH:14]=[N:13][CH:12]=[CH:11]2)=[O:5].[CH3:17][Mg]Br>C1COCC1>[CH:14]1[C:15]2[C:10](=[CH:9][CH:8]=[CH:7][C:6]=2[C:4](=[O:5])[CH3:17])[CH:11]=[CH:12][N:13]=1A solution of N-methoxy-N-methylisoquinoline-8-carboxamide (1.04 g, 4.81 mmol) in THF (40.1 ml) at 0° C. was treated with methylmagnesium bromide (11.22 ml, 33.7 mmol) in THF. Reaction was stirred at 0° C. for 1 hours before quenching with a saturated ammonium chloride solution (5 mL). After reaching RT, solution extracted with EtOAc (3×75 mL). Combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. Purified by normal phase chromatography (0-50% EtOAc in hexane) to yield 1-(isoquinolin-8-yl)ethanone as an oil.
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