7-Methoxy-isoquinolin-1(2H)-one synthesis
- Product Name:7-Methoxy-isoquinolin-1(2H)-one
- CAS Number:16027-16-0
- Molecular formula:C10H9NO2
- Molecular Weight:175.18
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Yield: 78%
Reaction Conditions:
with sodium acetate;bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate in water;1,2-dichloro-ethane at 85; for 16 h;
Steps:
1 7-Methoxyisoquinolin-1(2H)-one (IIi)
To a suspension of 4.4 g (25.1 mmol, 1.0 eq.) of 7-methoxyisoquinoline 2-oxide in 40 mL of 1,2-dichloroethane was added 6.1 g (75.4 mmol, 2.0 eq.) of sodium acetate followed by 23.4 g (50.3 mmol, 2.0 eq.) of bromotripyrrolidinophosphonium hexafluorophosphate and 5 mL of water and the mixture was heated at 85 °C for 16 h. The mixture was allowed to cool to room temperature and the solvent was removed in vacuo. The residue resuspended in 50 mL of water and extracted with 3 x 50 mL of methylene chloride. The combined organic extracts were washed with 80 mL of brine, dried (Na2SO4), filtered and the solvent was removed in vacuo. The residue was triturated with 50 mL of methyl tert-butyl ether to provide 2.0 g (11.4 mmol, 78%) of 7-methoxyisoquinolin-1(2H)-one (IIi). LCMS: m/z found 176.1 [M+H]+, RT = 1.78 min; 1H NMR (300 MHz, DMSO-d6) d 11.19 (bs, 1H), 7.59-7.62 (m, 2H), 7.30-7.33 (m, 1H), 7.04 (t, 1H), 6.51 (d, 1H), 3.85 (s, 3H).
References:
ARBUTUS BIOPHARMA CORPORATION;ARBUTUS BIOPHARMA, INC.;COLE, Andrew G.;FAN, Yi;KULTGEN, Steven;MESAROS, Eugen WO2020/123674, 2020, A1 Location in patent:Page/Page column 292
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