Hydrochloric Acid → 9-Benzenesulfonyl-5-hydroxy-3-(1-methyl-1H-pyrazol-4-yl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 1505854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1505854
[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[C:18]([OH:19])[C:13]=3[C:12]3[CH:22]=[C:23](Br)[CH:24]=[N:25][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:27][N:28]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[N:29]1.Cl>C([O-])(=O)C.[K+].C(#N)C.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]>[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[C:18]([OH:19])[C:13]=3[C:12]3[CH:22]=[C:23]([C:31]4[CH:30]=[N:29][N:28]([CH3:27])[CH:32]=4)[CH:24]=[N:25][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 582664728-(Benzenesulfonyl)-12-bromo-3-hydroxy-5,8,10-triazatricyclo[7.4.0.02,7]trideca-1(9),2,4,6,10,12-hexaene-4-carbonitrile

Produkt 1

HCID 582663859-Benzenesulfonyl-5-hydroxy-3-(1-methyl-1H-pyrazol-4-yl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6342AcetonitrileLösungsmittelHCID 517044Potassium AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 9-benzenesulfonyl-3-bromo-5-hydroxy-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (500 mg, 1.16 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (500 mg, 2.40 mmol) and [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II) (200 mg, 0.25 mmol) in 2N aqueous potassium acetate (3.6 mL) and acetonitrile (7.2 mL) was heated under microwave irradiation at 140° C., for 30 minutes. The reaction mixture was allowed to cool to ambient temperature, 1M hydrochloric acid (7.5 mL) was added and the mixture was stirred at room temperature for 1 h. The resulting precipitate was collected by filtration, washed with acetonitrile (5 mL) and left to air dry to afford the title compound as a crude brown solid (500 mg, 99%). LCMS (Method G): RT=3.84 min, M+H+=431.

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with acetonitrile (5 mL)
  4. waitleft to air
  5. customdry

Quellen und Nachweise

ORD-Eintrag
ord-29140b9d7a5e489b9e5d3d4fd8e46c4e
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216980B2

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