반응 #171852

반응 방정식

ammonium chloride

n-Butyl lithium

2-chloro-6,7-dihydro-9-bromopyrido[3,2-b]thieno[2,3-d]oxepine

triisopropylborate

→

2-Chloro-6,7-dihydro-pyrido[3,2-b]thieno[2,3-d]oxepine-9-boronic acid

용매

hexane

tetrahydrofuran

water

반응 조건

후처리

1. 1
   workup.WAITThe mixture was kept at −76° C. for 20 min
2. 2
   추출The product was extracted with 150 ml of ethyl acetate
3. 3
   세척The organic layer was washed with 100 ml of water, 100 ml of brine
4. 4
   건조dried over anhydrous sodium sulfate
5. 5
   여과The solution was filtered
6. 6
   농축concentrated in vacuum
7. 7
   기타to afford a residue which
8. 8
   기타was then triturated with a mixture of hexane and ethyl ether (1:1)
9. 9
   여과A precipitate was filtered
10. 10
    세척washed with cold ethyl ether, hexane
11. 11
    기타dried in vacuum

실험 절차

4.77 ml (12 mmol) of 2.5 M n-Butyl lithium in hexane was added dropwise to a solution of 3166 mg (10.0 mmol) of 2-chloro-6,7-dihydro-9-bromopyrido[3,2-b]thieno[2,3-d]oxepine in 100 ml of tetrahydrofuran at −76° C. After stirring for 10 min, 3.21 ml (14.0 mmol) of triisopropylborate was added. The mixture was kept at −76° C. for 20 min, then 10 ml of saturated aqueous ammonium chloride were added and the mixture was mixed with 360 ml of water. The product was extracted with 150 ml of ethyl acetate. The organic layer was washed with 100 ml of water, 100 ml of brine and dried over anhydrous sodium sulfate. The solution was filtered and concentrated in vacuum to afford a residue which was then triturated with a mixture of hexane and ethyl ether (1:1). A precipitate was filtered, washed with cold ethyl ether, hexane and dried in vacuum to give 2-Chloro-6,7-dihydro-pyrido[3,2-b]thieno[2,3-d]oxepine-9-boronic acid. Yield 2.20 g (78%). MS: (ESI+)=282.1.

출처