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25218-99-9

25218-99-9 Structure

25218-99-9 Structure
IdentificationBack Directory
[Name]

N-(6-Bromopyridin-2-yl)acetamide
[CAS]

25218-99-9
[Synonyms]

SKL879
N-(6-Bromopyridin-2-yl)
2-Acetamido-6-bromopyridine
N-(6-Bromopyridin-2-yl)acetamide
AcetaMide,N-(6-broMo-2-pyridinyl)-
[Molecular Formula]

C7H7BrN2O
[MDL Number]

MFCD00234277
[MOL File]

25218-99-9.mol
[Molecular Weight]

215.05
Chemical PropertiesBack Directory
[Melting point ]

157.4 °C
[Boiling point ]

389.6±27.0 °C(Predicted)
[density ]

1.630±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,Room Temperature
[pka]

13.15±0.70(Predicted)
[Appearance]

White to off-white Solid
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302+H312+H332-H315-H319-H335
[Precautionary statements ]

P260-P280-P312
[HS Code ]

2933399990
Hazard InformationBack Directory
[Uses]

2-Acetamido-6-bromopyridine is a chemical reagent used in the synthesis of diarylureas used as allosteric modulators. Also used in the prouction of novel Bcl-Abl inhibitors with flexible linkers.
[Synthesis]

2-Amino-6-bromopyridine

19798-81-3

Acetyl chloride

75-36-5

N-(6-Bromopyridin-2-yl)acetamide

25218-99-9

I. General procedure for the synthesis of N-(6-bromopyridin-2-yl)acetamide: Step a: To a solution of 6-bromopyridin-2-amine (10 g, 0.060 mol) and triethylamine (Et3N, 25 g, 0.27 mol) in dichloromethane (CH2Cl2, 300 mL) was slowly added acetyl chloride (AcCl, 13 g, 0.17 mol) at 0°C. The reaction mixture was stirred overnight at room temperature. After completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate (EtOAc, 200 mL x 3). The organic layers were combined, dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under reduced pressure to afford N-(6-bromopyridin-2-yl)acetamide (88% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.15 (d, J = 8.0 Hz, 1H), 7.97 (brs, 1H), 7.55 (t, J = 8.0 Hz, 1H), 7.18 (d, J = 8.0 Hz, 1H), 2.19 (s, 3H).

[References]

[1] Patent: WO2012/119979, 2012, A1. Location in patent: Page/Page column 34-35
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 15, p. 4730 - 4743
[3] Patent: WO2008/141119, 2008, A2. Location in patent: Page/Page column 84
[4] Patent: US2004/92741, 2004, A1. Location in patent: Page 4
[5] Patent: US2009/176842, 2009, A1. Location in patent: Page/Page column 13
Spectrum DetailBack Directory
[Spectrum Detail]

N-(6-Bromopyridin-2-yl)acetamide(25218-99-9)1HNMR
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