2-Amino-6-chloro-N-methoxy-N-methyl-nicotinamide → (2-Amino-6-chloro-pyridin-3-yl)-(2-fluoro-phenyl)-methanone

HRID 30105

Reaktionsgleichung

[NH2:1][C:2]1[N:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:3]=1[C:4](N(OC)C)=[O:5].[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Li]>O1CCCC1>[NH2:1][C:2]1[C:3]([C:4]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[F:15])=[O:5])=[CH:10][CH:11]=[C:12]([Cl:14])[N:13]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

2-Amino-6-chloro-N-methoxy-N-methyl-nicotinamide (500 mg, 2.32 mmol, Example 3) was dissolved in anhydrous tetrahydrofuran (14 mL) and cooled to −78° C. A solution of 2-fluorophenyl lithium (4-6 equiv, freshly prepared following the same procedure as in Example 4) was added. The reaction was stirred at −78° C. for 1-3 hrs and quenched with aqueous ammonium chloride solution. The resulting mixture was extracted with ethyl acetate, washed with saturated sodium chloride, dried over sodium sulfate and evaporated in vacuo. The product was then purified on silica gel to give (2-Amino-6-chloro-pyridin-3-yl)-(2-fluoro-phenyl)-methanone as a white solid (445.5 mg, 77% yield). HRMS, observed: 250.0306, Calcd for M+: 250.0309.

Aufarbeitung

additionwas added
customquenched with aqueous ammonium chloride solution
extractionThe resulting mixture was extracted with ethyl acetate
washwashed with saturated sodium chloride
dry with materialdried over sodium sulfate
customevaporated in vacuo
customThe product was then purified on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-eaad9f2e5822467f90ef726934124adc
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07423051B2

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