تفاعل #88525

معادلة التفاعل

3-bromo-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile

ammonium formate

→

title compound

المردود 80.0%

9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile

المردود 80.0%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto cool
2. 2
   ترشيحfiltered over a pad of Celite
3. 3
   غسيلwashed with methylene chloride (200 mL)
4. 4
   تركيزThe filtrate was concentrated in vacuo
5. 5
   أخرىpurified by flash chromatography (silica, 120 g, ISCO, 5-45% ethyl acetate in heptane)

الإجراء التجريبي

A mixture of 3-bromo-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (5.6 g, 14 mmol), ammonium formate (8.8 g, 139 mmol), and zinc (9.1 g, 139 mmol) in tetrahydrofuran (85 mL) was heated at 75° C. for 10 hours. The reaction was allowed to cool, filtered over a pad of Celite, and washed with methylene chloride (200 mL). The filtrate was concentrated in vacuo and then purified by flash chromatography (silica, 120 g, ISCO, 5-45% ethyl acetate in heptane) to afford the title compound as a white solid (3.6 g, 80%). 1H NMR (400 MHz, CDCl3) δ 9.17 (s, 1H), 8.73 (dd, J=4.8, 1.5, 1H), 8.46 (dd, J=7.8, 1.5, 1 H), 8.39 (s, 1H), 7.39 (dd, J=7.8, 4.8, 1H), 6.01 (s, 2H), 3.60 (t, J=8.0, 2H), 0.93 (t, J=8.0, 2H), −0.09 (s, 9H).

المصدر