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(2-Bromo-pyridin-4-yl)carbamic acid tert-butyl ester

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(2-Bromo-pyridin-4-yl)carbamic acid tert-butyl ester Basic information
Product Name:(2-Bromo-pyridin-4-yl)carbamic acid tert-butyl ester
Synonyms:4-(BOC-AMINO)-2-BROMOPYRIDINE;2-BROMO-4-BOC PYRIDINE;2-Bromo-4-(tert-butoxycarbonylamino)pyridine;N-Boc-4-amino-2-bromopyridine;Tert-butyl 2-bromopyridin-4-ylcarbamate;Zinc02511835;tert-butyl N-(2-broMopyridin-4-yl)carbaMate;(2-BROMO-PYRIDIN-4-Y
CAS:433711-95-6
MF:C10H13BrN2O2
MW:273.13
EINECS:
Product Categories:Heterocycle-Pyridine series
Mol File:433711-95-6.mol
(2-Bromo-pyridin-4-yl)carbamic acid tert-butyl ester Structure
(2-Bromo-pyridin-4-yl)carbamic acid tert-butyl ester Chemical Properties
Boiling point 299.3±25.0 °C(Predicted)
density 1.453±0.06 g/cm3(Predicted)
storage temp. 2-8°C
pka11.97±0.70(Predicted)
AppearanceWhite to off-white Solid
CAS DataBase Reference433711-95-6(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 22
Safety Statements 24/25
WGK Germany 3
HazardClass IRRITANT
MSDS Information
ProviderLanguage
ALFA English
(2-Bromo-pyridin-4-yl)carbamic acid tert-butyl ester Usage And Synthesis
Synthesis
4-Amino-2-bromopyridine

7598-35-8

Di-tert-butyl dicarbonate

24424-99-5

(2-BROMO-PYRIDIN-4-YL)CARBAMIC ACID TERT-BUTYL ESTER

433711-95-6

General procedure for the synthesis of 4-tert-butoxycarbonylamino-2-bromopyridine from 4-amino-2-bromopyridine and di-tert-butyl dicarbonate: 2-bromopyridin-4-amine (100.0 g), triethylamine (Et3N, 64.8 g), and dichloromethane (DCM, 1.0 L) were added to the reaction vial and the reaction mixture was stirred for 15-30 min at 20-30 °C. Subsequently, 4-dimethylaminopyridine (DMAP, 3.5 g) was added to the reaction vial and di-tert-butyl dicarbonate ((Boc)2O, 416.3 g) was added slowly and dropwise. The reaction mixture was stirred continuously at 20-30 °C for 16 h, during which the progress of the reaction was monitored by HPLC. After completion of the reaction, the reaction mixture was washed with deionized water (2 L). The organic phase was separated and concentrated under reduced pressure to give the crude product as a yellow solid. The solid was stirred with methanol (MeOH, 300.0 mL) at 20-30 °C for 30 min and then filtered to give 4-tert-butoxycarbonylamino-2-bromopyridine (171.2 g) as an off-white solid.

References[1] Dalton Transactions, 2016, vol. 45, # 32, p. 12807 - 12813
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 24, p. 8709 - 8715
[3] Patent: US2003/119847, 2003, A1
[4] Patent: WO2017/137535, 2017, A1. Location in patent: Page/Page column 105
(2-Bromo-pyridin-4-yl)carbamic acid tert-butyl ester Preparation Products And Raw materials
Raw materials2-Bromo-4-nitropyridine-->4-Amino-2-bromopyridine-->Di-tert-butyl dicarbonate-->4-Dimethylaminopyridine-->Triethylamine-->Dichloromethane
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