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

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

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

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

N-(6-Bromopyridin-2-yl)acetamide Chemical Properties,Usage,Production

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

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