反応 #172126

反応方程式

product

Methyl 3-bromobenzo[b]thiophene-2-carboxylate

acrylonitrile

tri-tert-butylphosphine

N-methyldicyclohexylamine

→

title compound

(E)-Methyl 3-(2-cyanovinyl)benzo[b]thiophene-2-carboxylate

溶媒

1,4-dioxane

toluene

ethyl acetate

反応条件

後処理

1. 1
   その他In a flask under nitrogen was placed
2. 2
   温度cooled
3. 3
   workup.STIRRINGstirred for 15 minutes
4. 4
   ろ過The mixture was filtered
5. 5
   洗浄the precipitate washed with 25 mL of ethyl acetate
6. 6
   濃縮The filtrate was concentrated

実験手順

In a flask under nitrogen was placed tris(dibenzylideneacetone)dipalladium(0) (313 mg, 0.34 mmol) in 25 mL of 1,4-dioxane followed by the product obtained from Example 97A (4.5 g, 16.7 mmol), N-methyldicyclohexylamine (3.91 g, 20.0 mmol), tri-tert-butylphosphine (0.68 mL of a 1.0 M solution in toluene, 0.68 mmol) and acrylonitrile (1.06 g, 20.0 mmol). The mixture was stirred and heated at 50° C. under nitrogen for 90 minutes and then cooled and diluted with 100 mL of ethyl acetate and stirred for 15 minutes. The mixture was filtered and the precipitate washed with 25 mL of ethyl acetate. The filtrate was concentrated and worked up as described in Example 55B to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.92 (s, 3H) 6.55 (d, J=17.29 Hz, 1H) 7.54-7.66 (m, 2H) 8.13-8.25 (m, 3H).

出典