Dichloromethane → 4-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-chloro-N-cyclohexylpyridin-2-amine

HRID 2089026Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2089026
[Br:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[CH:9][N:8]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1.Cl[CH2:22][Cl:23].C(=O)(O)[O-].[Na+].C(O[CH2:33][CH3:34])(=O)C>CN(C)C=O.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:3]3[CH:2]=[C:22]([Cl:23])[N:6]=[C:5]([NH:8][CH:34]4[CH2:33][CH2:17][CH2:16][CH2:15][CH2:20]4)[CH:4]=3)=[CH:9][N:8]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 242292401-Benzenesulfonyl-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 866498714-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-chloro-N-cyclohexylpyridin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 5-bromo-3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.155 g, 2.49 mmol), Example 168a (0.924 g, 2.74 mmol), catalytic amount of [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), complex with dichloromethane (1:1) and saturated sodium bicarbonate solution (6 mL) in 24 mL dimethylformamide was heated at 65° C. for 30 minutes. The material was cooled to room temperature, diluted with ethyl acetate, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified on silica gel using flash chromatography (6% ethyl acetate/hexane) to afford 0.68 g of the title compound. m/z 547.4 (APCI, M+H)+.

Aufarbeitung

  1. customwas heated at 65° C. for 30 minutes
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel using flash chromatography (6% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-2d027f35779b451cbfd67127525f9c7d
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08435980B2

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