تفاعل #438286

معادلة التفاعل

Water

N-(4-Cyano-2-iodo-5-trifluoromethyl-phenyl)-methanesulfonamide

tert-Butyl-(1,1-dimethyl-prop-2-ynyloxy)-dimethyl-silane

NEt3

→

solid

المردود 16.0%

2-[1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-trifluoromethyl-1H-indole-5-carbonitrile

المردود 16.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   استخلاصthe mixture was extracted twice with ethyl acetate
2. 2
   غسيلThe organic layers were washed with 10% LiCl solution
3. 3
   تجفيفdried over magnesium sulfate
4. 4
   ترشيحfiltered
5. 5
   أخرىevaporated to a brown oil
6. 6
   أخرىThe brown oil was purified by column chromatography
7. 7
   غسيلeluting with 1, 3, and 10% ethyl acetate/hexanes

الإجراء التجريبي

N-(4-Cyano-2-iodo-5-trifluoromethyl-phenyl)-methanesulfonamide (1.95 g, 5.0 mmol), tert-Butyl-(1,1-dimethyl-prop-2-ynyloxy)-dimethyl-silane (992 mg, 5.0 mmol), PdCl2(PPh3)2, (175 mg, 0.25 mmol), CuI (95 mg, 0.5 mmol), NEt3 (1.4 mL, 10.0 mmol), was mixed in DMF (15 mL) and stirred at room temperature for 16 hours. Water was added and the mixture was extracted twice with ethyl acetate. The organic layers were washed with 10% LiCl solution, dried over magnesium sulfate, filtered, evaporated to a brown oil. The brown oil was purified by column chromatography eluting with 1, 3, and 10% ethyl acetate/hexanes. The product was obtained as a white solid (306 mg, 16%). 1H NMR (CDCl3) δ 8.75 (s, 1H), 7.92 S, 1H), 7.67 (s, 1H), 6.27 (d, J=1.2 Hz, 1H), 1.58 (s, 6H), 0.85 (s, 9H), 0.3 (s, 6H). MS (m/z): 405 (MNa+), 381 (MH−).

المصدر