1-Bromo-3-(propylsulfonyl)benzene → Tert-butyl[(6-methyl-2-{[3-(propylsulfonyl)phenyl]ethynyl}pyridin-3-yl)oxy]acetate

HRID 2390173Notes

Reaction equation

HRID 2390173 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[C:10]([C:16]#[CH:17])=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[CH:21]=1>>[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[C:10]([C:16]#[C:17][C:24]2[CH:25]=[CH:20][CH:21]=[C:22]([S:26]([CH2:29][CH2:30][CH3:31])(=[O:27])=[O:28])[CH:23]=2)=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 565942651-Bromo-3-(propylsulfonyl)benzene2×HCID 58521986tert-Butyl [(2-ethynyl-6-methylpyridin-3-yl)oxy]acetate2×

Product 1

HCID 58522036Tert-butyl[(6-methyl-2-{[3-(propylsulfonyl)phenyl]ethynyl}pyridin-3-yl)oxy]acetate

Procedure

Following the general method as outlined in Intermediate 20, starting from (2-ethynyl-6-methyl-pyridin-3-yloxy)-acetic acid tert-butyl ester (Intermediate 86) and 1-bromo-3-(propane-1-sulfonyl)-benzene (Intermediate 5), the title compound was obtained as a yellow sticky solid after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-adb6f403d4af45ecbfb8d6a3d066bc14
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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