HuagongsheHuagongshe Chemistry Print Report · For research reference only
(4-Bromo-2,6-difluorophenyl)trimethylsilane → (S)-((S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl)(3,5-difluoro-4-(trimethylsilyl)phenyl)methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (4-Bromo-2,6-difluorophenyl)trimethylsilane | HCID 11543513 | — |
| Reactant | (S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehyde | HCID 86662512 | — |
| Reactant | Bromine magnesium | HCID 131730664 | — |
| Reactant | HCID 178461733 | HCID 178461733 | — |
| Product | (S)-((S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl)(3,5-difluoro-4-(trimethylsilyl)phenyl)methanol | HCID 66761564 | — |
Reaction Steps
Obtained by starting from (S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehyde and (4-bromo-2,6-difluorophenyl)trimethylsilane. Isopropylmagnesiumchloride-lithium chloride-complex (1.3 M in tetrahydrofurane) is used instead of isopropylmagnesium chloride. The bromine-magnesium exchange is performed at room temperature for 18 hours and at 40° C. for 4 hours.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09029544B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-6838ae52bad6422d8de263ab34e21bd8 |
| Source note | uspto-grants-2015_05 |