ChemicalBook CAS DataBase List tert-Butyl (4-broMopyridin-2-yl)(Methyl)carbaMate

tert-Butyl (4-broMopyridin-2-yl)(Methyl)carbaMate synthesis

8synthesis methods

Product Name:tert-Butyl (4-broMopyridin-2-yl)(Methyl)carbaMate
CAS Number:946000-13-1
Molecular formula:C11H15BrN2O2
Molecular Weight:287.15

207799-10-8

74-88-4

tert-Butyl (4-broMopyridin-2-yl)(Methyl)carbaMate

946000-13-1

Step 1: Tert-butyl (4-bromopyridin-2-yl) carbamate (0.25 g, 0.915 mmol) was dissolved in DMF (5 ml) at 0 °C. To this solution, NaH (60% oil solution, 0.073 g, 1.83 mmol) was slowly added, keeping the reaction mixture stirred at 0°C for 15 min. Subsequently, methyl iodide (0.26 g, 1.37 mmol) was added at the same temperature. The reaction mixture was transferred to room temperature and stirring was continued for 1 hour. After completion of the reaction, the mixture was poured into ice-cold water (20 ml) and extracted with EtOAc (2 x 15 ml). The organic layers were combined, washed with brine (20 ml) and then dried over Na2SO4. After filtration, the organic phase was concentrated under reduced pressure to afford the crude product (tert-butyl (4-bromopyridin-2-yl)(methyl)carbamate (0.25 g, 0.87 mmol), which was used in the subsequent reaction without further purification.The LCMS analysis (Method A) showed a retention time of 2.50 min, and the mass spectra (MS: ES+) observed the peaks with m/z of 230.9 and 232.9 (M -56) ion peaks.

207799-10-8 Synthesis

207799-10-8
147 suppliers
$11.00/250mg

74-88-4
356 suppliers
$15.00/10g

946000-13-1
16 suppliers
$71.00/50mg

Yield:946000-13-1 76%

Reaction Conditions:

Stage #1: (4-bromopyridin-2-yl)-carbamic acid tert-butyl esterwith sodium hydride in tetrahydrofuran at 0; for 0.25 h;
Stage #2: methyl iodine in tetrahydrofuran at 0 - 20; for 16 h;

Steps:

tert-Butyl (4-bromo-pyridin-2-yl)-methyl-carbamate (160)To a solution of te/7-butyl carbamate 155 (300 mg, 1.10 mmol) in THF (5 mL) at 0^°C is added sodium hydride (53 mg, 1.32 mmol, 60% dispersion in mineral oil) in one portion. After stirring 15 minutes, iodomethane is added (82 μL, 1.32 mmol) and the reaction mixture warmed to RT and stirred 16 h. The reaction is then quenched with 5% citric acid (10 mL) and extracted into EtOAc (2 x 10 mL). The EPO combined organic phases are dried over Na₂SO₄ and purified by column chromatography (70% EtOAc in heptane) to give the title compound. Yield: 240 mg (76%). LC/MS t_r 1.62 min. MS(ES+) m/z 289, 287 (M+H), 233, 231 (M-C(CH₃)₃+H).

References:

WO2008/57497,2008,A2 Location in patent:Page/Page column 296-297