Sodium hydride → {2-[4-(6-Cyanopyridin-2-yloxy)phenyl]ethyl}carbamic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[C:21]1[N:26]=[C:25]([C:27]#[N:28])[CH:24]=[CH:23][CH:22]=1>>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:21]2[CH:22]=[CH:23][CH:24]=[C:25]([C:27]#[N:28])[N:26]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]Participants
4
Procedure
Using a method similar to Example 381 Part A, using [2-(4-hydroxyphenyl)ethyl]carbamic acid tert-butyl ester (0.140 g, 0.588 mmol), NaH (80% in mineral oil) (0.194 g. 0.647 mmol) and 6-bromopyridine-2-carbonitrile (0.107 g, 0.588 mmol) gives the title compound (0.0895 g, 44.8%): MS ES+ 340.2 (M+H)+, base peak MS ES+ 284.0 (M+2H—C(CH3)3)+, MS ES− 338.3 (M−H)−; TLC [silica gel 60 F254, 40% ethyl acetate in hexanes] Rf=0.24.
Sources & evidence
- ORD record
- ord-8ef242290d03401bb4e4c0d53baf4ec3
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07381719B2
Reaction notes
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