반응 #68960

반응 방정식

9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene

hydrogen chloride

5-(8-Bromoisoquinolin-3-ylamino)pyrazine-2-carbonitrile

benzophenone imine

caesium carbonate

→

title compound

수율 11.0%

5-(8-Aminoisoquinolin-3-ylamino)pyrazine-2-carbonitrile

수율 11.0%

용매

toluene

DMF

THF

반응 조건

후처리

1. 1
   기타was degassed under a stream of nitrogen gas
2. 2
   기타the mixture was degassed for a further 5 minutes
3. 3
   온도Upon cooling the reaction mixture
4. 4
   workup.ADDITIONwas diluted with ethyl acetate
5. 5
   여과filtered through celite
6. 6
   세척washed sequentially with water and brine
7. 7
   건조then dried (Na2SO4)
8. 8
   농축concentrated to dryness
9. 9
   기타to afford a brown oil
10. 10
    농축concentrated to dryness

실험 절차

A mixture of tris(dibenzylideneacetone)dipalladium (0) (18 mg, 0.020 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (23 mg, 0.040 mmol) in toluene (1 mL) and DMF (1 mL) was degassed under a stream of nitrogen gas with stirring for 15 minutes. 5-(8-Bromoisoquinolin-3-ylamino)pyrazine-2-carbonitrile (65 mg, 0.20 mmol), benzophenone imine (36 mg, 0.20 mmol) and caesium carbonate (130 mg, 0.40 mmol) were added and the mixture was degassed for a further 5 minutes, then heated at 140° C. for 40 minutes in a microwave reactor. Upon cooling the reaction mixture was diluted with ethyl acetate and filtered through celite, washed sequentially with water and brine then dried (Na2SO4) and concentrated to dryness to afford a brown oil. The residue was dissolved in THF (2 mL) and treated with aqueous hydrogen chloride (2 mL, 2M) for 30 minutes and then concentrated to dryness. Preparative HPLC gave the title compound (5.64 mg, 0.022 mmol, 11%). 1H NMR (d6-DMSO, 400 MHz) δ 10.90 (br s, 1H), 9.35 (s, 1H), 8.80 (s, 1H), 8.70 (s, 1H), 8.25 (s, 1H), 7.40 (t, 1H, J=7.8, 6.8 Hz), 6.95 (d, 1H, J=7.8 Hz), 6.60 (d, 1H, J=6.8 Hz), 6.25 (s, 1H). LC-MS (2) Rt=2.32 min; m/z (ESI+) 263 (M+H).

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