تفاعل #1111586

معادلة التفاعل

triethylsilylacetylene

lithium chloride

Na2CO3

40

5-Chloro-3-iodo-pyridin-2-ylamine

→

desired product 41

المردود 44.0%

5-Chloro-2-(triethyl-silanyl)-1H-pyrrolo[2,3-b]pyridine

المردود 44.0%

المذيبات

DMF

—

ethyl acetate-ether

ظروف التفاعل

المعالجة

1. 1
   غسيلthe organic phase washed with water and brine
2. 2
   تجفيفthen dried (Na2SO4)
3. 3
   تركيزconcentrated in vacuo

الإجراء التجريبي

A mixture of 40 (9.5 g, 37.3 mmol) was dissolved in 320 mL of DMF and triethylsilylacetylene (20 mL, 112 mmol), Pd2Cl2 (dppf)2 (1.52 g, 1.9 mmol), lithium chloride (1.58 g, 37.3 mmol) and 2M Na2CO3 (7.9 mL, 74.7 mL) were added and the mixture was stirred and refluxed at 90° C. for 15 h under nitrogen. Diluted with ethyl acetate-ether mixture (1:1) and the organic phase washed with water and brine then dried (Na2SO4) and concentrated in vacuo. The residue was subjected to flash chromatography (20% EtOAc/80% hexanes) to give 4.37 g (44%) of the desired product 41. 1H NMR (500 MHz, CDCl3) 9.4 (bs, 1H), 8.2 (s, 1H), 7.9 (s, 1H), 6.6 (s, 1H), 0.9 (t, 9H), 0.75 (q, 6H).

المصدر