1,2-Dichloroethane → methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrimido[5,4-b]indole-4-carboxylate

HRID 2410736

Reaktionsgleichung

Reaktionsgleichung von HRID 2410736
ClCCCl.[N:5]([C:8]1[C:9]([C:30]([O:32][CH3:33])=[O:31])=[N:10][C:11]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[N:12][C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=[N+]=[N-]>ClCCl.CCOC(C)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.[Rh].[Rh]>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]2[C:13]3[N:12]=[C:11]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[N:10]=[C:9]([C:30]([O:32][CH3:33])=[O:31])[C:8]=3[NH:5][C:19]=2[CH:18]=1

Komponenten

6

Edukt 2

HCID 111,2-DichloroethaneHCID 86663016Methyl 5-azido-2,6-bis(4-methoxyphenyl)pyrimidine-4-carboxylate

Produkt 1

HCID 66605466methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrimido[5,4-b]indole-4-carboxylateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6099591Rhodium(II) Octanoate DimerKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

1,2-Dichloroethane (0.25 mL) was added to a mixture of methyl 5-azido-2,6-bis(4-methoxyphenyl)pyrimidine-4-carboxylate (154 mg, 0.393 mmol), rhodium octanoate dimer (31 mg, 0.039 mmol) and crushed 4 A° molecular sieves (154 mg) in a microwave vial. The vial was sealed and heated at 60° C. overnight. This was diluted with mixture of dichloromethane and EtOAc (9:1), filtered, and the solvent removed from the filtrate. Radial silica chromatography (step gradient elution with methylene chloride containing 0 to 5% EtOAc) afforded methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrimido[5,4-b]indole-4-carboxylate (100 mg) as a yellow solid. MS (ESI) m/z 364.0 (M+H). 1H NMR (DMSO-d6) δ ppm 11.68 (1H, s), 8.48 (2H, d, J=8.85 Hz), 8.23 (1H, d, J=8.85 Hz), 7.24 (1H, d, J=2.14 Hz), 7.11 (2H, d, J=8.85 Hz), 6.99 (1H, dd, J=8.85, 2.14 Hz), 4.09 (3H, s), 3.93 (3H, s), 3.86 (3H, s).

Aufarbeitung

  1. customcrushed 4 A° molecular sieves (154 mg) in a microwave vial
  2. customThe vial was sealed
  3. filtrationfiltered
  4. customthe solvent removed from the filtrate
  5. washRadial silica chromatography (step gradient elution with methylene chloride containing 0 to 5% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-139c99fff70c4a7facda872425d14f07
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815840B2

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