Potassium Carbonate → 4-{5-Chloro-2-[(trimethylsilyl)ethynyl]phenyl}-2-methoxypyridine

HRID 56637Notes

Reaction equation

HRID 56637 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]#[C:10][Si:11]([CH3:14])([CH3:13])[CH3:12].[CH3:15][O:16][C:17]1[CH:22]=[C:21](B(O)O)[CH:20]=[CH:19][N:18]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([C:9]#[C:10][Si:11]([CH3:14])([CH3:13])[CH3:12])=[C:2]([C:21]2[CH:20]=[CH:19][N:18]=[C:17]([O:16][CH3:15])[CH:22]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23546919(2-Methoxypyridin-4-yl)boronic acidHCID 1020785952-Bromo-4-chloro-1-[2-(trimethylsilyl)ethynyl]benzene

Product 1

HCID 1233889294-{5-Chloro-2-[(trimethylsilyl)ethynyl]phenyl}-2-methoxypyridine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 333 mg (1.16 mmol) of [(2-bromo-4-chlorophenyl)ethynyl](trimethyl)silane, 195 mg (1.28 mmol, 1.1 eq.) of (2-methoxypyridin-4-yl)boronic acid, 401 mg (2.9 mmol, 2.5 eq.) of potassium carbonate and 14 mg (0.02 mmol, 0.015 eq.) of [1,1-bis(diphenylphosphino)ferrocene]palladium(II) chloride/monodichloromethane adduct in 18 ml of dioxane was irradiated in a microwave at 130° C. for 15 min. The reaction mixture was then filtered through Celite and the residue was washed with dioxane. The combined filtrates were concentrated under reduced pressure. After addition of water/ethyl acetate and phase separation, the organic phase was concentrated under reduced pressure. Yield: 550 mg (purity 41%, 62% of theory)

Workup

  1. filtrationThe reaction mixture was then filtered through Celite
  2. washthe residue was washed with dioxane
  3. concentrationThe combined filtrates were concentrated under reduced pressure
  4. additionAfter addition of water/ethyl acetate and phase separation
  5. concentrationthe organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9bdb4e2f02ed4cfaba6cf5dfe78e68af
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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