تفاعل #67117

معادلة التفاعل

1,1-dimethylethyl 4-[4-cyano-1-(phenylsulfonyl)-1H-indazol-6-yl]-1H-indole-1-carboxylate

toluene

dibutyl(oxo)stannane

trimethylsilyl azide

→

title compound

المردود 33.0%

6-(1H-Indol-4-yl)-1-(phenylsulfonyl)-4-(1H-tetrazol-5-yl)-1H-indazole

المردود 33.0%

المذيبات

acetic acid

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to room temperature
2. 2
   تركيزconcentrated in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in methanol/DCM
4. 4
   أخرىpreabsorbed onto silica (20 g)
5. 5
   غسيلeluted with 0-40% methanol in DCM
6. 6
   workup.ADDITIONThe product containing fraction
7. 7
   أخرىwas evaporated
8. 8
   أخرىto give a green foam which
9. 9
   درجة الحرارةthe mixture heated to 100° C. overnight
10. 10
    درجة الحرارةThe mixture was heated for a further 24 h
11. 11
    درجة الحرارةcooled to room temperature
12. 12
    أخرىA precipitate formed
13. 13
    ترشيحwhich was collected by filtration and air
14. 14
    أخرىdried over the weekend

الإجراء التجريبي

To a round bottomed flask was charged 1,1-dimethylethyl 4-[4-cyano-1-(phenylsulfonyl)-1H-indazol-6-yl]-1H-indole-1-carboxylate (6.16 g, 12.36 mmol) followed by toluene (250 ml). The resulting solution was then treated with dibutyl(oxo)stannane (0.554 g, 2.224 mmol) and trimethylsilyl azide (3.3 ml, 25.09 mmol). The mixture was heated to 90° C. overnight, then cooled to room temperature and concentrated in vacuo. The residue was dissolved in methanol/DCM and preabsorbed onto silica (20 g). This was placed on the top of a silica cartridge (750 g) and eluted with 0-40% methanol in DCM. The product containing fraction was evaporated to give a green foam which was placed into acetic acid (50 ml) and the mixture heated to 100° C. overnight. The mixture was heated for a further 24 h, then cooled to room temperature and water (250 ml) added. A precipitate formed, which was collected by filtration and air dried over the weekend to give the title compound as a pale grey solid (1.8 g).

المصدر