Tert-butyl[(3-bromo-5-chloropyridin-2-yl)oxy]acetate → Tert-butyl[(5-chloro-3-{[2-fluoro-5-(propylsulfonyl)phenyl]ethynyl}pyridin-2-yl)oxy]acetate

HRID 2390242Notes

Reaction equation

HRID 2390242 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[C:14](Br)=[CH:13][C:12]([Cl:16])=[CH:11][N:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:18]([C:20]1[CH:25]=[C:24]([S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[CH:23]=[CH:22][C:21]=1[F:32])#[CH:19]>>[C:1]([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[C:14]([C:19]#[C:18][C:20]2[CH:25]=[C:24]([S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[CH:23]=[CH:22][C:21]=2[F:32])=[CH:13][C:12]([Cl:16])=[CH:11][N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 58521889Tert-butyl[(3-bromo-5-chloropyridin-2-yl)oxy]acetate3×HCID 585219352-Ethynyl-1-fluoro-4-(propylsulfonyl)benzene2×

Product 1

HCID 58521925Tert-butyl[(5-chloro-3-{[2-fluoro-5-(propylsulfonyl)phenyl]ethynyl}pyridin-2-yl)oxy]acetate

Procedure

Following the general method as outlined in Intermediate 182, starting from tert-butyl[(3-bromo-5-chloropyridin-2-yl)oxy]acetate (Intermediate 183) and 2-ethynyl-1-fluoro-4-(propane-1-sulfonyl)-benzene (Intermediate 109), 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-f44db42ebf5d41a6a5803a95e9f9907f
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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