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

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tert-Butyl (4-broMopyridin-2-yl)(Methyl)carbaMate Basic information
Product Name:tert-Butyl (4-broMopyridin-2-yl)(Methyl)carbaMate
Synonyms:tert-Butyl (4-broMopyridin-2-yl)(Methyl)carbaMate;(4-BROMO-PYRIDIN-2-YLMETHYL)-CARBAMIC ACID TERT-BUTYL ESTER;tert-Butyl N-(4-bromopyridin-2-yl)-N-methylcarbamate;Carbamic acid, N-(4-bromo-2-pyridinyl)-N-methyl-, 1,1-dimethylethyl ester
CAS:946000-13-1
MF:C11H15BrN2O2
MW:287.15
EINECS:
Product Categories:
Mol File:946000-13-1.mol
tert-Butyl (4-broMopyridin-2-yl)(Methyl)carbaMate Structure
tert-Butyl (4-broMopyridin-2-yl)(Methyl)carbaMate Chemical Properties
Boiling point 348.8±27.0 °C(Predicted)
density 1.391±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
pka3.60±0.10(Predicted)
AppearanceWhite to off-white Solid
Safety Information
MSDS Information
tert-Butyl (4-broMopyridin-2-yl)(Methyl)carbaMate Usage And Synthesis
Synthesis
TERT-BUTYL 4-BROMOPYRIDIN-2-YLCARBAMATE

207799-10-8

Iodomethane

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.

References[1] Patent: WO2008/57497, 2008, A2. Location in patent: Page/Page column 296-297
[2] Patent: WO2007/89669, 2007, A2. Location in patent: Page/Page column 208
[3] Patent: WO2008/57469, 2008, A1. Location in patent: Page/Page column 296-297
[4] Patent: WO2008/57468, 2008, A1. Location in patent: Page/Page column 296-297
[5] Patent: WO2016/46530, 2016, A1. Location in patent: Page/Page column 79
tert-Butyl (4-broMopyridin-2-yl)(Methyl)carbaMate Preparation Products And Raw materials
Raw materialsSodium hydride-->N,N-Dimethylformamide-->tert-Butyl 4-bromopyridin-2-ylcarbamate-->Mineral oil-->Iodomethane
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