ChemicalBook--->CAS DataBase List--->1188477-11-3

1188477-11-3

1188477-11-3 Structure

1188477-11-3 Structure
IdentificationBack Directory
[Name]

Tert-Butyl5-Bromopyridin-2-yl(methyl)carbamate
[CAS]

1188477-11-3
[Synonyms]

Tert-Butyl5-Bromopyridin-2-yl(methyl)carbamate
Carbamic acid, N-[(5-bromo-2-pyridinyl)methyl]-, 1,1-dimethylethyl ester
[Molecular Formula]

C11H15BrN2O2
[MDL Number]

MFCD11520868
[MOL File]

1188477-11-3.mol
[Molecular Weight]

287.15
Chemical PropertiesBack Directory
[Boiling point ]

372.4±32.0 °C(Predicted)
[density ]

1.367±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C
[pka]

11.14±0.46(Predicted)
[Appearance]

White to light yellow Solid
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H317-H319-H335
[Precautionary statements ]

P261-P280-P305+P351+P338
Spectrum DetailBack Directory
[Spectrum Detail]

Tert-Butyl5-Bromopyridin-2-yl(methyl)carbamate(1188477-11-3)1HNMR
Hazard InformationBack Directory
[Synthesis]

Di-tert-butyl dicarbonate

24424-99-5

5-Bromo-2-pyridinecarbonitrile

97483-77-7

Tert-Butyl5-Bromopyridin-2-yl(methyl)carbamate

1188477-11-3

GENERAL STEPS: To a solution of 5-bromo-2-cyanopyridine (3.0 g, 16.4 mmol) in methanol (60 mL) was sequentially added di-tert-butyl dicarbonate (7.2 g, 32.8 mmol) and nickel chloride hexahydrate (0.33 g, 1.64 mmol). The reaction mixture was cooled to 0 °C, followed by the addition of sodium borohydride (4.3 g, 0.115 mol) in batches over a period of 2 hours. The reaction mixture was continued to be stirred at 15 °C for 1 h, after which it was poured into ice water (200 g) and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by fast column chromatography to afford the target product tert-butyl (5-bromopyridin-2-ylmethyl)carbamate (2.2 g, 47% yield) as a yellow solid. m/z 287,289 ([M+H]+) by LC-MS.

[References]

[1] Patent: WO2016/112088, 2016, A1. Location in patent: Paragraph 0660
[2] Patent: US2013/237502, 2013, A1. Location in patent: Paragraph 0367
[3] Patent: WO2018/42342, 2018, A1. Location in patent: Page/Page column 53
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