3-Bromo-4-methylpyridine → Tert-butyl{4-cyano-2-[(4-methylpyridin-3-yl)ethynyl]phenoxy}acetate

HRID 2390151Notes

Reaction equation

HRID 2390151 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[C:17]#[CH:18])([CH3:4])([CH3:3])[CH3:2].Br[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][C:26]=1[CH3:27]>>[C:1]([O:5][C:6](=[O:19])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[C:17]#[C:18][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][C:26]=1[CH3:27])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 8176303-Bromo-4-methylpyridineHCID 58522073Tert-butyl(4-cyano-2-ethynylphenoxy)acetate2×

Product 1

HCID 58522020Tert-butyl{4-cyano-2-[(4-methylpyridin-3-yl)ethynyl]phenoxy}acetate

Procedure

Following the general method as outlined in Intermediate 20, starting from tert-butyl(4-cyano-2-ethynylphenoxy)acetate (Intermediate 46) and 3-bromo-4-methylpyridine (53), the title compound was obtained as a dark orange sticky solid after purification by flash column chromatography, eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-c8578c97095c40b098d31e227974835b
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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