Tert-butyl{4-chloro-2-[(trimethylsilyl)ethynyl]phenoxy}acetate → Tert-butyl {[2-(trimethylsilyl-1-ethynyl)-6-methylpyridin-3-yl]oxy}acetate

HRID 2390171Notes

Reaction equation

HRID 2390171 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12](Cl)=[CH:11][C:10]=1[C:16]#[C:17][Si:18]([CH3:21])([CH3:20])[CH3:19])([CH3:4])([CH3:3])[CH3:2].C(OC(=O)COC1C(Br)=[N:33]C(C)=CC=1)(C)(C)C>>[CH3:19][Si:18]([C:17]#[C:16][C:10]1[C:9]([O:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:22])=[CH:14][CH:13]=[C:12]([CH3:11])[N:33]=1)([CH3:21])[CH3:20]

Participants

3

Reactant 2

HCID 56594380Tert-butyl{4-chloro-2-[(trimethylsilyl)ethynyl]phenoxy}acetateHCID 58522063Tert-butyl 2-[(2-bromo-6-methyl-3-pyridinyl)oxy]acetate2×

Product 1

HCID 58521867Tert-butyl {[2-(trimethylsilyl-1-ethynyl)-6-methylpyridin-3-yl]oxy}acetate

Procedure

Following the general method as outlined in Intermediate 2, starting from tert-butyl[(2-bromo-6-methylpyridin-3-yl)oxy]acetate (Intermediate 84), the title compound was obtained as a brown oil after purification by flash column chromatography (silica), eluting with petroleum ether and ethyl acetate (98:2).

Sources & evidence

ORD record
ord-2658e31aefe24acba0b6035f4b214b5d
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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