Triethylamine → 6-(2-fluorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

HRID 1025630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1025630
C([N:4]1[C:8]2=[N:9][C:10](Br)=[CH:11][CH:12]=[C:7]2[C:6]([C:14]#[N:15])=[CH:5]1)(=O)C.C(N(CC)CC)C.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[F:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=1B(O)O>O1CCOCC1>[F:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=1[C:10]1[N:9]=[C:8]2[NH:4][CH:5]=[C:6]([C:14]#[N:15])[C:7]2=[CH:12][CH:11]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 27343542-Fluorophenylboronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 747882791-Acetyl-6-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

Produkt 1

HCID 710086026-(2-fluorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrileAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a 100 mL round-bottomed flask, 1-acetyl-6-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (250 mg, 947 μmol, Eq: 1.00), triethylamine (575 mg, 792 μl, 5.68 mmol, Eq: 6) and X-PHOS (181 mg, 379 μmol, Eq: 0.40) were combined with dioxane (25.0 ml) to give a colorless solution. [1,1′-bis(diphenylphosphino)ferrocene]dichloropaladium(II) (173 mg, 237 μmol, Eq: 0.25) and 2-fluorophenylboronic acid (265 mg, 1.89 mmol) were added and the resultant mixture was degassed for 5 minutes under Nitrogen. The reaction mixture was heated to 100° C. and microwaved for 1 hr. The reaction mixture was poured into 50 mL EtOAc and washed with H2O. The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 40 g, 20% to 30% EtOAc in hexanes) to give 6-(2-fluorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (220 mg, 98%).

Aufarbeitung

  1. customto give a colorless solution
  2. customthe resultant mixture was degassed for 5 minutes under Nitrogen
  3. custommicrowaved for 1 hr
  4. additionThe reaction mixture was poured into 50 mL EtOAc
  5. washwashed with H2O
  6. dry with materialThe organic layers were dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by flash chromatography (silica gel, 40 g, 20% to 30% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-975cc9966e4444738df746d5ec127978
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729078B2

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