2-Bromo-5-(trifluoromethyl)pyridine → (R)-((S)-5'-(tert-butyldimethylsilyloxy)-4'-iodo-2'-isopropyl-6',8'-dihydro-5'H-spiro[cyclobutane-1,7'-quinoline]-3'-yl)(5-(trifluoromethyl)pyridin-2-yl)methanol

HRID 573759Notes

Reaction equation

HRID 573759 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:18][C:17]2([CH2:21][CH2:20][CH2:19]2)[CH2:16][C:15]2[N:14]=[C:13]([CH:22]([CH3:24])[CH3:23])[C:12]([CH:25]=[O:26])=[C:11]([I:27])[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:29]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][N:30]=1>>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]2([CH2:21][CH2:20][CH2:19]2)[CH2:16][C:15]2[N:14]=[C:13]([CH:22]([CH3:23])[CH3:24])[C:12]([C@H:25]([C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][N:30]=3)[OH:26])=[C:11]([I:27])[C:10]1=2)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 27364342-Bromo-5-(trifluoromethyl)pyridineHCID 86662517(S)-5'-(tert-butyldimethylsilyloxy)-4'-iodo-2'-isopropyl-6',8'-dihydro-5'H-spiro[cyclobutane-1,7'-quinoline]-3'-carbaldehyde

Product 1

HCID 66761792(R)-((S)-5'-(tert-butyldimethylsilyloxy)-4'-iodo-2'-isopropyl-6',8'-dihydro-5'H-spiro[cyclobutane-1,7'-quinoline]-3'-yl)(5-(trifluoromethyl)pyridin-2-yl)methanol

Procedure

Obtained by starting from (S)-5′-(tert-butyldimethylsilyloxy)-4′-iodo-2′-isopropyl-6′,8′-dihydro-5′H-spiro[cyclobutane-1,7′-quinoline]-3′-carbaldehyde and 2-bromo-5-(trifluoromethyl)pyridine.

Workup

  1. customObtained

Sources & evidence

ORD record
ord-2b2b27446a0440f19b7b18782ad619c1
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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