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Water → 3-Fluoro-5-[(4-fluorophenyl)methyl]-2-pyridinecarbonitrile

HRID 2364525
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Reaktionsgleichung

Reaktionsgleichung von HRID 2364525
[F:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6](I)[CH:7]=1.[Cl-].[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][Zn+])=[CH:15][CH:14]=1.O.C(OCC)(=O)C>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6]([CH2:17][C:16]2[CH:19]=[CH:20][C:13]([F:12])=[CH:14][CH:15]=2)[CH:7]=1
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Komponenten

7

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 210758683-Fluoro-5-iodopicolinonitrileHCID 178505764HCID 178505764, Verbindung

Produkt 1

HCID 694815193-Fluoro-5-[(4-fluorophenyl)methyl]-2-pyridinecarbonitrileAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-fluoro-5-iodo-2-pyridinecarbonitrile(2.31 g, 9.3 mmol) in THF (100 mL) was added 4-fluorobenzyl zinc chloride (27.9 mL, 0.5 M in THF, 14.0 mmol) followed by Pd(PPh3)4 (538 mg, 0.47 mmol). The resultant solution was heated at 75° C. (bath temperature) for 3 hours. After cooling to room temperature, water and ethyl acetate were added. The layers were separated and the organic layer was washed with brine. The aqueous layer was acidified with 1 N HCl until it cleared and extracted with ethyl acetate. The combined organics were dried over sodium sulphate. Filtration and concentration followed by purification by silica gel chromatography provided 3-fluoro-5-[(4-fluorophenyl)methyl]-2-pyridinecarbonitrile (1.6 g, 75%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.40 (s, 1 H), 7.28 (d, J=8.8 Hz, 1 H), 7.12 (dd, J=8.4, 5.2 Hz, 2 H), 7.03 (t, J=8.4 Hz, 2 H), 4.04 (s, 2 H). MS m/z 231 (M+1).

Aufarbeitung

  1. customThe layers were separated
  2. washthe organic layer was washed with brine
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organics were dried over sodium sulphate
  5. filtrationFiltration and concentration
  6. customfollowed by purification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3e717676fa2f47f39c4df560e48c9800
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08691991B2

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