Methyl iodide → HCID 68182222, compound

Participants

Reaction Steps

To a solution of 6,7-dimethoxy-1-methylisoquinolin-3-ol CCH 18060 (603 mg, 2.75 mmol) in acetic acid (27 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise bromine (0.15 mL, 2.92 mmol) and the mixture was stirred for 2 h at RT. The solid was then filtered and washed with acetic acid (20 mL), EtOAc (30 mL), Et2O (4×7 mL), CH2Cl2 (55 mL), saturated NaHCO3 (15 mL) and finally with H2O (10 mL). After drying under vacuum, a yellow solid was obtained (718 mg). This solid (500 mg, 1.68 mmol) was dissolved in acetone (20 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer before addition of Cs2CO3 (550 mg, 1.69 mmol). The mixture was stirred for 20 min at RT, MeI (1.0 mL, 16.06 mmol) was added and the mixture was stirred for 4.5 h at RT. After addition of SiO2 (3.0 g), the residue was filtered and washed several times with a mixture of cyclohexane:EtOAc=90:10 (until all the desired product was eluted). The filtrate was then concentrated to dryness at 40° C. under vacuum to give 4-bromo-3,6,7-trimethoxy-1-methylisoquinoline SMA 44070 as a yellow solid (139 mg, 23% yield).

Provenance & Evidence