Potassium Carbonate → 2-{[6-(Morpholin-4-ylmethyl)pyridin-2-yl]amino}-5-pyridin-3-ylthiophene-3-carbonitrile

HRID 386135Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 386135
[NH2:1][C:2]1[S:3][C:4]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][C:6]=1[C:7]#[N:8].Br[C:16]1[N:21]=[C:20]([CH2:22][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:19]=[CH:18][CH:17]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>C(O)(CC)(C)C>[N:23]1([CH2:22][C:20]2[N:21]=[C:16]([NH:1][C:2]3[S:3][C:4]([C:9]4[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=4)=[CH:5][C:6]=3[C:7]#[N:8])[CH:17]=[CH:18][CH:19]=2)[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 234381474-((6-Bromopyridin-2-yl)methyl)morpholineHCID 686716452-Amino-5-pyridin-3-ylthiophene-3-carbonitrile

Produkt 1

HCID 686714272-{[6-(Morpholin-4-ylmethyl)pyridin-2-yl]amino}-5-pyridin-3-ylthiophene-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 64052-Methyl-2-butanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-Amino-5-pyridin-3-ylthiophene-3-carbonitrile (76 mg, 0.38 mmol), 4-[(6-bromopyridin-2-yl)methyl]morpholine (Example 45, Step 1) (97 mg, 0.38 mmol), dibenyzlideneacetone bis(triphenylphosphine) (17.29 mg, 0.02 mmol), 2-dicylohexylphosphino-2′,4′,6′-triisopropyl-1,1-biphenyl (45.0 mg, 0.09 mmol), and potassium carbonate (57.4 mg, 0.42 mmol) were dissolved in tert-amyl alcohol (3.8 ml) and the mixture was bubbled with nitrogen for 5 min. The reaction was then heated to 100° C. overnight. The mixture was diluted with ethyl acetate and water and extracted with ethyl acetate (3×50 mL). The combined organics were washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with dichloromethane/methanol to afford the title compound as a solid.

Aufarbeitung

  1. customthe mixture was bubbled with nitrogen for 5 min
  2. additionThe mixture was diluted with ethyl acetate and water
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe combined organics were washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel
  9. washeluting with dichloromethane/methanol

Quellen und Nachweise

ORD-Eintrag
ord-b933f44bc8504ab4ac58ca4d258c67f4
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

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