Triethylamine → 1-(3,4-Methylenedioxyphenyl)-2-[5-(3-pyridinyl)-pyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-beta-carboline

HRID 988325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 988325
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23]3[N:28]=[CH:27][C:26](Br)=[CH:25][N:24]=3)=[CH:4][C:3]=2[O:2]1.[N:30]1[CH:35]=[CH:34][CH:33]=[C:32](B(O)O)[CH:31]=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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]>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23]3[N:28]=[CH:27][C:26]([C:32]4[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=4)=[CH:25][N:24]=3)=[CH:4][C:3]=2[O:2]1

Komponenten

8

Edukt 3

HCID 8471TriethylamineHCID 27343783-Pyridinylboronic acidHCID 226403241-(3,4-Methylenedioxyphenyl)-2-(5-bromopyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-beta-carboline

Produkt 1

HCID 226403091-(3,4-Methylenedioxyphenyl)-2-[5-(3-pyridinyl)-pyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-beta-carboline

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A stirred mixture of palladium(II) acetate (27 mg, 0.12 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (dppf) (83 mg, 0.15 mmol) in dry DMF (20 ml) was warmed to 50° C. for 15 min and then cooled. 1-(3,4-methylenedioxyphenyl)-2-(5-bromopyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-β-carboline (674 mg, 1.5 mmol) (prepared as in Example 52), pyridine-3-boronic acid (203 mg, 1.7 mmol) and triethylamine (0.3 ml, 2.1 mmol) were added to the solution and the mixture heated to 90° C. for 16 h. The solution was diluted with ethyl acetate and filtered through filter paper. The organic phase was washed with brine and water, then dried over Na2SO4. A small amount of silica gel was added into the solution and the solution was dried in vacuo. Purification by flash column (silica gel, hexane:ethyl acetate=1:1, v/v, followed by hexane:ethyl acetate=1:2, v/v) yielded the product as a white solid.

Aufarbeitung

  1. temperaturecooled
  2. temperaturethe mixture heated to 90° C. for 16 h
  3. filtrationfiltered
  4. filtrationthrough filter paper
  5. washThe organic phase was washed with brine and water
  6. dry with materialdried over Na2SO4
  7. additionA small amount of silica gel was added into the solution
  8. customthe solution was dried in vacuo
  9. customPurification by flash column (silica gel, hexane

Quellen und Nachweise

ORD-Eintrag
ord-4985829a03d146738dfacf1d8ca3cf45
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06635638B2

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