Ethyl 3-(trimethylsilyl)propynoate → 1-(5-Bromopyridin-2-yl)-1-(2,6-difluorophenyl)-4-(trimethylsilyl)but-3-yn-2-one

HRID 1454976Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=2[F:16])=[N:6][CH:7]=1.[CH3:17][Si:18]([CH3:27])([CH3:26])[C:19]#[C:20][C:21](OCC)=[O:22]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:9]2[C:10]([F:16])=[CH:11][CH:12]=[CH:13][C:14]=2[F:15])[C:21](=[O:22])[C:20]#[C:19][Si:18]([CH3:27])([CH3:26])[CH3:17])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-bromo-2-(2,6-difluorobenzyl)pyridine (5.6 g) in THF was added ethyl 3-(trimethylsily)propynoate (4.2 mL) and LHMD (42 mL, 1N in THF) at −78° C. The mixture was warmed to 0° C. and stirred in additional 2 h. The reaction was complete by TLC and quenched with NH4Cl, extracted with ethyl acetate. The organic layer was washed with water, brine, dried over MgSO4 and condensed in vacuo. The crude compound was purified by silica gel (hexanes/methylene chloride) to give the desired product.

Workup

customquenched with NH4Cl
extractionextracted with ethyl acetate
washThe organic layer was washed with water, brine
dry with materialdried over MgSO4 and condensed in vacuo
customThe crude compound was purified by silica gel (hexanes/methylene chloride)

Sources & evidence

ORD record: ord-bae2a9105a944a8293550526683bebbf
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482345B2

Reaction notes

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