7-bromo-6-methoxyIsoquinoline synthesis
- Product Name:7-bromo-6-methoxyIsoquinoline
- CAS Number:666735-07-5
- Molecular formula:C10H8BrNO
- Molecular Weight:238.08
Yield:666735-07-5 42.31%
Reaction Conditions:
Stage #1: chloroformic acid ethyl ester;(3-bromo-4-methoxyphenyl)-methylidene(2,2-dimethoxyethyl)amine in tetrahydrofuran at 0; for 0.0833333 h;
Stage #2: with triethyl phosphite in tetrahydrofuran at 0 - 20; for 18 h;
Stage #3: with titanium tetrachloride in chloroform; for 48 h;Reflux;
Steps:
101 Synthesis of Intermediate B188
To a stirred solution of (Z)-[(3-bromo-4-methoxyphenyl)methylidene](2,2- dimethoxyethyl)amine (9 g, 29.785 mmol, 1.00 equiv) in THF (50 mL) was added ethyl chloroformate (3.23 g, 29.785 mmol, 1.00 equiv) dropwise at 0 . The reaction mixture was stirred for 5 min, then triethyl phosphite (5.94 g, 35.742 mmol, 1.2 equiv) was added dropwise. The resulting mixture was stirred for 18 h at room temperature. The solvents were removed in vacuo, and excess reagent was removed by forming an azeotrope with toluene (50 mL) and concentrating the resulting mixture under reduced pressure to give a residue. The residue was combined with titanium tetrachloride (22.60 g, 119.140 mmol, 4.0 equiv) and CHCl3 (50 mL). The resulting mixture was heated to reflux for 48 h, then poured on ice and adjusted to pH 9 using aqueous ammonia. The resulting mixture was extracted with ethyl acetate (3 x 200 mL). The organic layers were combined, washed with brine (1x100 mL), dried over anhydrous Na2SO4, and filtered. After filtration, the filtrate was concentrated under reduced pressure to afford 7-bromo-6-methoxyisoquinoline (3 g, 42.31%) as a solid. LCMS (ES, m/z): 238 [M+H]+
References:
WO2022/6550,2022,A1 Location in patent:Page/Page column 420-421
![Ethanamine, N-[(3-bromo-4-methoxyphenyl)methylene]-2,2-dimethoxy-](/CAS/20200611/GIF/918492-64-5.gif)
918492-64-5
0 suppliers
inquiry
666735-07-5
31 suppliers
inquiry
34841-06-0
245 suppliers
$8.00/5g
22483-09-6
498 suppliers
$5.00/5g
666735-07-5
31 suppliers
inquiry
34841-06-0
245 suppliers
$8.00/5g
666735-07-5
31 suppliers
inquiry