تفاعل #421652

معادلة التفاعل

3-amino-5-bromo pyridine

5-bromopyridin-3-amine

pivaloyl chloride

→

N-(5-bromopyridin-3-yl)pivalamide

المردود 73.1%

المذيبات

pyridine

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirred for 30 min
2. 2
   ترشيحThe precipitate was filtered
3. 3
   غسيلwashed with cold water
4. 4
   أخرىdried at room temperature

الإجراء التجريبي

To a solution of 3-amino-5-bromo pyridine (XXV) (1.0 g, 5.78 mmol) in dry pyridine (10 mL) was added pivaloyl chloride (XXVIII) (769 mg, 6.38 mmol). The reaction mixture was stirred at room temperature for 3 h. The reaction was poured into an ice water/saturated aqueous NaHCO3 mixture and stirred for 30 min. The precipitate was filtered, washed with cold water and dried at room temperature to yield N-(5-bromopyridin-3-yl)pivalamide (XXIX) as an off-white solid (1.082 g, 4.22 mmol, 73.1% yield). 1H NMR (DMSO-d6, 500 MHz) δ ppm 1.23 (s, 9H), 8.37 (d, J=2 Hz, 1H), 8.39 (t, J=2 Hz, 1H), 8.80 (d, J=2 Hz, 1H), 9.58 (brs, 1H); ESIMS found C10H13BrN2O m/z 257.0 (M+H).

المصدر