Dichloromethane → 4-[3-(2-Methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N-methyl-benzamide

HRID 1171124

Reaktionsgleichung

Reaktionsgleichung von HRID 1171124
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:19][NH:20][C:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)=[O:22].ClCCl>C(#N)C.C([O-])(O)=O.[Na+].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]>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:26]3[CH:27]=[CH:28][C:23]([C:21]([NH:20][CH3:19])=[O:22])=[CH:24][CH:25]=3)[CH:3]=2)[NH:8][N:9]=1

Komponenten

7

Edukt 3

HCID 6344DichloromethaneHCID 27735264-(Methylcarbamoyl)benzeneboronic acidHCID 178489372HCID 178489372, Verbindung

Produkt 1

HCID 1784852994-[3-(2-Methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N-methyl-benzamideAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6342AcetonitrileLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a solution of 5-bromo-3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridine (26 mg, 0.085 mmol) in acetonitrile (1 mL) and saturated aqueous NaHCO3 (1 mL) in a microwave vial was added 4-(N-methylaminocarbonyl)phenylboronic acid (17 mg, 0.094 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II), complex with dichloromethane (1:1) (3.5 mg, 0.004 mmol). The vial was capped, flushed with N2, evacuated under vacuum, and heated in a microwave at 130° C. for 1800 seconds. The material was extracted into EtOAc and the organic layer was dried over Na2SO4. The material was adsorbed onto SiO2 and purified by flash chromatography in a EtOAc (containing 10% MeOH) and hexane gradient. The clean fractions were concentrated via rotary evaporation to afford the title compound as a white powder (5.9 mg, 20% yield). 1H NMR (500 MHz, CD3OD) δ 8.85 (s, 1H), 8.41 (s, 1H), 7.94 (d, J=8.5 Hz, 2H), 7.78 (d, J=8.5 Hz, 2H), 7.67 (d, J=7.5 Hz, 1H), 7.48 (t, 7.0 Hz, 1H), 7.21 (d, J=8.5 Hz, 1H), 7.11 (t, J=7.0 Hz, 1H), 3.89 (s, 3H), 2.95 (s, 3H). MS: m/z 359.1 [M+H+].

Aufarbeitung

  1. customThe vial was capped
  2. customflushed with N2
  3. customevacuated under vacuum
  4. extractionThe material was extracted into EtOAc
  5. dry with materialthe organic layer was dried over Na2SO4
  6. custompurified by flash chromatography in a EtOAc (containing 10% MeOH) and hexane gradient
  7. concentrationThe clean fractions were concentrated via rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-b2a04ac00fdb48a48ce95285506cd811
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829558B2

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