Sodium hydride → N-[(2-chloropyridin-3-yl)methyl]-N-pyridin-3-ylpyridin-3-amine

HRID 563947

Reaktionsgleichung

Reaktionsgleichung von HRID 563947
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=1.[H-].[Na+].Br[CH2:17][C:18]1[C:19]([Cl:24])=[N:20][CH:21]=[CH:22][CH:23]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:24][C:19]1[C:18]([CH2:17][N:7]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:23][CH:22]=[CH:21][N:20]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 598775N-pyridin-3-ylpyridin-3-amineHCID 189310283-(Bromomethyl)-2-chloropyridine

Produkt 1

HCID 59138879N-[(2-chloropyridin-3-yl)methyl]-N-pyridin-3-ylpyridin-3-amineAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-pyridin-3-ylpyridin-3-amine (510 mg, 3 mmol) in anhydrous DMF (4.5 mL) was added 60% sodium hydride/mineral oil (169 mg, 4.2 mmol). After stirring at ambient temperature for 15 min., 3-(bromomethyl)-2-chloropyridine (677 mg, 3.28 mmol) (preparation described in U.S. Pat. No. 5,739,326) was added neat and the action was stirred for ˜2 hours. The reaction was diluted with ethyl acetate, washed with NaHCO3 solution, then water, and the organic layer was dried over anhydrous sodium sulfate, filtered, and the solvent evaporated. The residue was purified by silica gel chromato-graphy eluting with a 20-90% acetonelhexane gradient to give the purified product which upon trituration with diethyl ether gave the title compound as a tan solid (684 mg, 77% yield). 1H-NMR (500 MHz , CDCl3): δ 8.40 (2H, d, J=2.7 Hz), 8.34 (1H, d, J=4.6 Hz), 8.30 (2H, d, J=4.6 Hz), 7.69 (1H, d, J=7.8 Hz), 7.33-7.35 (2H, br d, J=˜8.3 Hz), 7.20-7.26 (4H, m), 5.04 (2H, s). m/e (m+1): 297.0

Aufarbeitung

  1. addition5,739,326) was added neat
  2. stirringthe action was stirred for ˜2 hours
  3. washwashed with NaHCO3 solution
  4. dry with materialwater, and the organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe residue was purified by silica gel chromato-graphy
  8. washeluting with a 20-90% acetonelhexane gradient
  9. customto give the purified product which upon trituration with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-c65ed67f66f942c183feac62d2d24622
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067607B2

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