6-Tert-butyl-2-chloropyridine-3-carbonitrile → 6-tert-Butyl-2-(3,3-dimethylbut-1-ynyl)-5-methylnicotinonitrile

HRID 921054Notes

Reaction equation

HRID 921054 reaction equation
[C:1]([C:5]1[C:12]([CH3:13])=[CH:11][C:8]([C:9]#[N:10])=[C:7](Cl)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].ClC1C(C#N)=C[CH:19]=[C:18]([C:24]([CH3:27])([CH3:26])[CH3:25])N=1>>[C:1]([C:5]1[C:12]([CH3:13])=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:19]#[C:18][C:24]([CH3:27])([CH3:26])[CH3:25])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 532788766-Tert-butyl-2-chloropyridine-3-carbonitrileHCID 866802626-Tert-butyl-2-chloro-5-methylnicotinonitrile

Product 1

HCID 679954326-tert-Butyl-2-(3,3-dimethylbut-1-ynyl)-5-methylnicotinonitrile

Procedure

Procedure analogous to 31, using 62.6 g (300 mmol) of 6-tert-butyl-2-chloro-5-methylnicotinonitrile, S79, instead of 194.7 g (1 mol) of 2-chloro-3-cyano-6-tert-butylpyridine, S28, and scaling the remaining reagents correspondingly on a molar level. Yield: 68.9 g (271 mmol), 90%. Purity: >95% according to 1H-NMR.

Sources & evidence

ORD record
ord-06371eb4b0ea4c74a78aa7aba78c49f8
Source dataset
uspto-grants-2016_03
Patent number
US09273080B2

Reaction notes

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