Dichloromethane → 4-Benzo[b]thiophen-7-yl-2-fluoro-5-methyl-pyridine

HRID 422103

Reaktionsgleichung

[F:1][C:2]1[CH:7]=[C:6](I)[C:5]([CH3:9])=[CH:4][N:3]=1.[S:10]1[CH:14]=[CH:13][C:12]2[CH:15]=[CH:16][CH:17]=[C:18](B3OC(C)(C)C(C)(C)O3)[C:11]1=2.ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl.C(O)(C)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C1COCC1>[S:10]1[CH:14]=[CH:13][C:12]2[CH:15]=[CH:16][CH:17]=[C:18]([C:6]3[C:5]([CH3:9])=[CH:4][N:3]=[C:2]([F:1])[CH:7]=3)[C:11]1=2

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

In a flask, combine 2-fluoro-4-iodo-5-methyl-pyridine (355 mg, 1.5 mmol), 2-benzo[b]thiophen-7-yl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (282 mg, 1.8 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (61 mg, 0.07 mmol), 2-(di-tert-butylphosphino)biphenyl (13 mg, 0.04 mmol), sodium carbonate (2 M, 1.5 mL, 3 mmol) and THF (10 mL). Heat the mixture at 100° C. for 3 hours in an oil bath. Dilute the mixture with chloroform/isopropanol (3/1). Wash the solution with saturated aqueous sodium chloride. Dry over sodium sulfate. Concentrate in vacuo to a dark residue. Purify by column chromatography (20% ethyl acetate in hexane) to afford the title compound (300 mg, 82%) as yellow oil. MS (ES) m/z 244 [M+1]+.

Aufarbeitung

customIn a flask, combine
washWash the solution with saturated aqueous sodium chloride
dry with materialDry over sodium sulfate
concentrationConcentrate in vacuo to a dark residue
customPurify by column chromatography (20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag: ord-67153add23f04a72b4d18cb246fd63c5
Quelldatensatz: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08101628B2

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