(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

HRID 573711Notes

Reaction equation

HRID 573711 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]([CH3:23])[CH3:22])[C:12]([CH:24]=[O:25])=[C:11]([I:26])[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:28]1[CH:33]=[C:32]([F:34])[C:31]([Si:35]([CH3:38])([CH3:37])[CH3:36])=[C:30]([F:39])[CH:29]=1.C([Mg]Cl)(C)C.[Cl-].[Li+].BrBr.[Mg]>>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:19])([CH3:20])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]([CH3:22])[CH3:23])[C:12]([C@H:24]([C:28]3[CH:29]=[C:30]([F:39])[C:31]([Si:35]([CH3:37])([CH3:36])[CH3:38])=[C:32]([F:34])[CH:33]=3)[OH:25])=[C:11]([I:26])[C:10]1=2)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 11543513(4-Bromo-2,6-difluorophenyl)trimethylsilaneHCID 86662512(S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehydeHCID 131730664Bromine magnesiumHCID 178461733HCID 178461733, compound

Product 1

HCID 66761564(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

Procedure

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.

Workup

  1. customObtained

Sources & evidence

ORD record
ord-6838ae52bad6422d8de263ab34e21bd8
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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