تفاعل #318035

معادلة التفاعل

Intermediate 37

1,1-Dimethylethyl [(6-iodo-4-{[3-(methyloxy)phenyl]amino}-3-quinolinyl)carbonyl]carbamate

4-{[tert-butyl(dimethyl)silyl]oxy} benzenethiol

(oxydi-2,1-phenylene)bis(diphenylphosphine)

potassium tert-butoxide

→

title compound

المردود 46.4%

6-[(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)thio]-4-[(3-methoxyphenyl)amino]quinoline-3-carboxamide

المردود 46.4%

المذيبات

ethyl acetate

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was cooled
2. 2
   غسيلwashed with a sodium carbonate solution (30 ml)
3. 3
   غسيلThe organic extracts were washed with water (30 ml)
4. 4
   تجفيفdried (Na2SO4)
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىThe residue was purified by chromatography on silica gel
7. 7
   تركيزThe appropriate fractions were concentrated in vacuo

الإجراء التجريبي

A stirred mixture of Intermediate 37 (0.8 g) and 4-{[tert-butyl(dimethyl)silyl]oxy} benzenethiol (0.74 g, EP465802A1), with (oxydi-2,1-phenylene)bis(diphenylphosphine) (0.05 g), potassium tert-butoxide (0.26 g) and tris(dibenzylideneacetone) dipalladium(0) (0.08 g) in toluene (30 ml) was heated at 106° C. for 18 h. The mixture was cooled, diluted with ethyl acetate (25 ml) and washed with a sodium carbonate solution (30 ml). The organic extracts were washed with water (30 ml) , dried (Na2SO4) and concentrated in vacuo. The residue was purified by chromatography on silica gel using ethyl acetate/diethyl ether (7:3) as the eluent. The appropriate fractions were concentrated in vacuo to give the title compound as a yellow foam (0.38 g).

المصدر