(3-Bromopropoxy)(tert-butyl)dimethylsilane → HCID 86682462, compound

HRID 715881Notes

Reaction equation

HRID 715881 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[F:13][C:14]1([F:58])[CH2:19][CH2:18][CH:17]([C:20]2[C:29]3[CH:28]([OH:30])[CH2:27][C:26]([CH3:32])([CH3:31])[CH2:25][C:24]=3[N:23]=[C:22]([CH:33]3[CH2:38][CH2:37][N:36]([C:39]4[N:44]=[CH:43][C:42]([OH:45])=[CH:41][N:40]=4)[CH2:35][CH2:34]3)[C:21]=2[CH:46]([F:57])[C:47]2[CH:52]=[CH:51][C:50]([C:53]([F:56])([F:55])[F:54])=[CH:49][CH:48]=2)[CH2:16][CH2:15]1>>[Si:6]([O:5][CH2:4][CH2:3][CH2:2][O:45][C:42]1[CH:41]=[N:40][C:39]([N:36]2[CH2:35][CH2:34][CH:33]([C:22]3[C:21]([CH:46]([F:57])[C:47]4[CH:52]=[CH:51][C:50]([C:53]([F:54])([F:55])[F:56])=[CH:49][CH:48]=4)=[C:20]([CH:17]4[CH2:18][CH2:19][C:14]([F:13])([F:58])[CH2:15][CH2:16]4)[C:29]4[CH:28]([OH:30])[CH2:27][C:26]([CH3:32])([CH3:31])[CH2:25][C:24]=4[N:23]=3)[CH2:38][CH2:37]2)=[N:44][CH:43]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

3

Reactant 2

HCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 76372263(-)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-[1-(5-hydroxypyrimidin-2-yl)piperidin-4-yl]-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol

Product 1

HCID 86682462HCID 86682462, compound

Procedure

Reactions similar to those of Example 13 were performed except for using (3-bromopropoxy) (tert-butyl)dimethylsilane instead of ethyl iodide, and from 61 mg (94 μmol) of (−)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-[1-(5-hydroxypyrimidin-2-yl)piperidin-4-yl]-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol, which was prepared by a method similar to that of Example 4, 71 mg (87 μmol) of 2-{1-[5-(3-{[tert-Butyl(dimethyl)silyl]oxy}propoxy)pyrimidin-2-yl]piperidin-4-yl}-4-(4,4-difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol was obtained.

Sources & evidence

ORD record
ord-9f866e38afdf453ab9b7c99d2acd7004
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

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