반응 #425753

반응 방정식

4-(3-(tert-Butoxycarbonyl)phenyl)-3-methylpyridine 1-oxide

4-Methylbenzene-1-sulfonyl chloride

Ethanolamine

→

product

수율 36.3%

tert-Butyl 3-(2-amino-5-methylpyridin-4-yl)benzoate

수율 36.3%

용매

pyridine

acetonitrile

반응 조건

후처리

1. 1
   workup.STIRRINGto stir for 5 minutes at room temperature
2. 2
   기타The crude product was partitioned between dichloromethane
3. 3
   기타The layers were separated
4. 4
   세척the organic layer was washed with a saturated aqueous solution of sodium chloride
5. 5
   건조The organic layer was dried over sodium sulfate
6. 6
   기타purified on 40 g of silica gel utilizing a gradient of 0-100% ethyl acetate in hexanes

실험 절차

4-(3-(tert-Butoxycarbonyl)phenyl)-3-methylpyridine 1-oxide (0.467 g, 1.64 mmol) was dissolved in a mixture of pyridine (0.53 mL) and acetonitrile (15 mL) under an atmosphere of argon. 4-Methylbenzene-1-sulfonyl chloride (0.406 g, 2.13 mmol) was added and the reaction mixture was stirred at 75° C. for 72 hours. Ethanolamine (7 mL) was then added and the reaction mixture was allowed to stir for 5 minutes at room temperature. The crude product was partitioned between dichloromethane and a saturated aqueous solution of sodium bicarbonate. The layers were separated and the organic layer was washed with a saturated aqueous solution of sodium chloride. The organic layer was dried over sodium sulfate and then purified on 40 g of silica gel utilizing a gradient of 0-100% ethyl acetate in hexanes to yield the pure product (0.169 g, 0.594 mmol, 36.3%). ESI-MS m/z calc. 284.2. found 285.1 (M+1)+. Retention time of 1.28 minutes. 1H NMR (400.0 MHz, DMSO-d6) δ 7.94-7.91 (m, 1H), 7.84 (s, 1H), 7.79 (d, J=1.7 Hz, 1H), 7.62-7.56 (m, 2H), 6.33 (s, 1H), 5.78 (s, 2H), 1.99 (s, 3H), 1.55 (s, 9H).

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