Sodium Carbonate → 5-(3,4-dimethoxy-phenyl)-3-phenyl-1H-pyrrolo[2,3-b]pyrazine

HRID 272057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272057
I[N:2]1[C:6]2[N:7]=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:9][NH:10][C:5]=2[CH:4]=[CH:3]1.[CH3:17][O:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26].C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+]>Cl[Pd-2](Cl)(P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.ClCCl.C(#N)C>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([N:2]2[C:6]3[N:7]=[C:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH2:9][NH:10][C:5]=3[CH:4]=[CH:3]2)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 27347023,4-Dimethoxyphenylboronic acidHCID 686183675-iodo-3-phenyl-1H-pyrrolo[2,3-b]pyrazine

Produkt 1

HCID 686173185-(3,4-dimethoxy-phenyl)-3-phenyl-1H-pyrrolo[2,3-b]pyrazineAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418903HCID 178418903, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

50 mg (0.16 mmol) of 5-iodo-3-phenyl-1H-pyrrolo[2,3-b]pyrazine, 38 mg (0.20 mmol) of 3,4-dimethoxyphenylboronic acid and 6 mg (5 mol %) of dichlorobis(triphenylphosphino)palladium(II) were placed in a vial and 1 ml of acetonitrile and 1 ml of a 2 M aqueous solution of sodium carbonate were added and the mixture irradiated in a Personal Chemistry®® microwave reactor to 165° C. for 1200 sec. The resulting mixture was distributed between 15 ml of a saturated aqueous solution of sodium bicarbonate and 75 ml of dichloromethane. The organic phase was dried over sodium sulfate and evaporated. The crude was purified via flash chromatography on silica gel using a gradient of methanol in dichloromethane. The product isolated was crystallized from hot ethanol to afford 14 mg (43 μmol, 27% yield) of 5-(3,4-dimethoxy-phenyl)-3-phenyl-1H-pyrrolo[2,3-b]pyrazine as an orange powder. 1H-NMR (d6-DMSO) δ: 12.30 [1H] s, 8.92 [1H] s, 8.43 [1H] s, 8.35 [2H] d, 7.80 [1H] (m), 7.79 [1H] d(m), 7.46 [2H] dd, 7.25 [1H] dd(d), 7.13 [1H] d, 3.92 [3H] s, 3.84 [3H] s. MS: m/z 332 [MH+].

Aufarbeitung

  1. additionwere added
  2. customthe mixture irradiated in a Personal Chemistry®® microwave reactor to 165° C. for 1200 sec
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated
  5. customThe crude was purified via flash chromatography on silica gel using a gradient of methanol in dichloromethane
  6. customThe product isolated
  7. customwas crystallized from hot ethanol

Quellen und Nachweise

ORD-Eintrag
ord-ef9de5f0b2334d6eb2726cfa64f4f10a
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452993B2

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