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ChemicalBook CAS DataBase List 2-BROMO-6-TERT-BUTYLPYRIDINE

2-BROMO-6-TERT-BUTYLPYRIDINE synthesis

5synthesis methods
-

Yield: 77%

Reaction Conditions:

with copper(l) iodide in tetrahydrofuran at 0 - 25; for 1 h;Inert atmosphere;

Steps:

1 Step 1 - 2-Bromo-6-tert-butyl-pyridine
To a solution of 2,6-dibromopyridine (3.00 g, 12.6 mmol, CAS 626-05-1) in THF (30 mL) was added CuI (120 mg, 633umol) followed by addition of tert-butyl(chloro)magnesium (1.7 M, 35.7 mL, CAS 677-22-5) at 0 °C. The reaction mixture was stirred at 25 °C for 1 hr. On completion, the mixture was quenched by NH4Cl aqueous (100 mL), then extracted with EA (3 X 100 mL). The organic phase was separated and washed with water (100 mL), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give the title compound (2.1 g, 77% yield) as yellow oil.1H NMR (400 MHz, DMSO-d6) d 7.73 -7.64 (m, 1H), 7.50 -7.41 (m, 2H), 1.29 (s, 9H).

References:

KYMERA THERAPEUTICS, INC.;MAINOLFI, Nello;JI, Nan;WEISS, Matthew M.;ZHENG, Xiaozhang;ZHANG, Yi;FLEMING, Paul R. WO2020/264499, 2020, A1 Location in patent:Paragraph 00920; 001832-001834