ChemicalBook CAS DataBase List 3-benzyl-6-bromo-2-methoxyquinoline

3-benzyl-6-bromo-2-methoxyquinoline synthesis

12synthesis methods

Product Name:3-benzyl-6-bromo-2-methoxyquinoline
CAS Number:654655-69-3
Molecular formula:C17H14BrNO
Molecular Weight:328.2

3-benzyl-6-bromo-2-methoxyquinoline is a quinoline derivative, which can be used as an intermediate of bedaquiline, a potential drug for the treatment of tuberculosis. 3-Benzyl-6-bromo-2-chloroquinoline and sodium methoxide in dry methanol were refluxed for 8h. The reaction solution was purified to obtain 3-benzyl-6-bromo-2-methoxyquinoline.

654655-68-2 Synthesis

654655-68-2
138 suppliers
$5.00/250mg

67-56-1 Synthesis

67-56-1
803 suppliers
$7.29/5ml-f

124-41-4 Synthesis

124-41-4
722 suppliers
$12.00/25g

654655-69-3
250 suppliers
$8.00/250mg

Yield:654655-69-3 89%

Reaction Conditions:

for 8 h;Heating / reflux;

Steps:

B
Preparation of 3 -Benzyl- 6-bromo-2-m ethoxy-q u m olin e; To a stirred solution of compound 3-Benzyl-6-bromo-2-chloro-qumolme (5 O g, 15 0 mmol) m dry methanol (50 ml) was added sodium methoxide (30% w/v m methanol, 15.0 ml, 84 0 mmol) and the contents were heated under reflux for 8 h The volatiles were removed under reduced pressure, poured into ice-water mixture, the solid separated out was filtered, washed with water and dried to furnish the compound (4 4 g, 89%) as an off-white solid, Mp 83-85⁰C ¹H NMR (400 MHz, CDCl₃). δ 4.02 (s, 2 H), 4 07 (s, 3 H), 7 20-7 26 (m, 3 H), 7 29-7 34 (m, 2 H), 7 47 (s, 1 H), 7 60 (dd, J = 8 0, 4 0 Hz, 1 H), 7 60 (dd, J = 8 8, 2 2 Hz, 1 H), 7.73 (d, J= 2.0 Hz, 1 H) (M+H)⁺= 328, 330

References:

CHATTOPADHYAYA, Jyoti;UPADHAYAYA, Ram Shankar WO2009/91324, 2009, A1 Location in patent:Page/Page column 23

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654655-68-2 Synthesis

654655-68-2
138 suppliers
$5.00/250mg

124-41-4 Synthesis

124-41-4
722 suppliers
$12.00/25g

654655-69-3
250 suppliers
$8.00/250mg

References