Potassium Phosphate, Tribasic → 2-(prop-1-en-2-yl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile

HRID 1852855

Reaktionsgleichung

Reaktionsgleichung von HRID 1852855
[N:1]1[C:9]2[CH:8]=[C:7]([C:10]#[N:11])[N:6]=[CH:5][C:4]=2[NH:3][CH:2]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:20][C:21]1(C)[C:25](C)(C)OB(C(C)=C)O1>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]>[CH2:20]=[C:21]([C:2]1[NH:3][C:4]2[CH:5]=[N:6][C:7]([C:10]#[N:11])=[CH:8][C:9]=2[N:1]=1)[CH3:25]

Komponenten

5

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 867245573H-imidazo[4,5-c]pyridine-6-carbonitrile

Produkt 1

HCID 867246012-(prop-1-en-2-yl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A vial was charged with the faster eluting enantiomer (enantiomer 1) of 2-bromo-4-(5-chloropyridin-3-yl)-3-[(1R or S)-1-(trans-4-methylcyclohexyl)ethyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (Example 4.1, Step 3; 150 mg, 0.33 mmol), potassium phosphate (208 mg, 0.98 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (23.9 mg, 0.033 mmol). The tube was evacuated and backfilled with argon (3×). Fully degassed dioxane (1.5 mL) and water (0.15 mL) were added, followed by 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (0.078 mL, 0.392 mmol). The vial was sealed and heated to 50° C. for 16 hours. The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes, linear gradient) to afford 4-(5-chloropyridin-3-yl)-3-[(1R or S)-1-(trans-4-methylcyclohexyl)ethyl]-2-(prop-1-en-2-yl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile. MS ESI calc'd. for C24H26ClN5 [M+H]+ 420. found 420.

Aufarbeitung

  1. additionA vial was charged with the
  2. customThe tube was evacuated
  3. additionFully degassed dioxane (1.5 mL) and water (0.15 mL) were added
  4. customThe vial was sealed
  5. temperatureThe reaction mixture was cooled to room temperature
  6. custompartitioned between water and ethyl acetate
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes, linear gradient)

Quellen und Nachweise

ORD-Eintrag
ord-437ea08e380b48f28c813739b3cc088b
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962611B2

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