Triisopropyl borate → HCID 57900174, compound

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.

1. waitThe mixture was kept at −76° C. for 20 min
2. extractionThe product was extracted with 150 ml of ethyl acetate
3. washThe organic layer was washed with 100 ml of water, 100 ml of brine
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationThe solution was filtered
6. concentrationconcentrated in vacuum
7. customto afford a residue which
8. customwas then triturated with a mixture of hexane and ethyl ether (1:1)
9. filtrationA precipitate was filtered
10. washwashed with cold ethyl ether, hexane
11. customdried in vacuum

ORD record

ord-3b088ac8acf54b8481868411bc490b66

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07928248B2