Triethylamine → tert-butyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate

HRID 45579

Reaktionsgleichung

Reaktionsgleichung von HRID 45579
C[Si]([C:5]#[CH:6])(C)C.C(N(CC)CC)C.I[C:15]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([C:24]3[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=3)[CH:22]=2)[N:17]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:16]=1.[CH2:37]([N:44]=[N+:45]=[N-:46])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1COCC1.CO.Cl[Pd](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.[Cu]I>[CH2:37]([N:44]1[CH:6]=[C:5]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([C:24]4[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=4)[CH:22]=3)[N:17]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:16]=2)[N:46]=[N:45]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 12152Benzyl azideHCID 66111TrimethylsilylacetyleneHCID 58217086Tert-butyl 3-iodo-5-(1-methyl-1H-pyrazol-4-YL)-1H-pyrrolo[2,3-B]pyridine-1-carboxylate

Produkt 1

HCID 66778317tert-butyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3.4 0.09 ml (0.63 mmol) of trimethylsilylacetylene and 0.12 ml (0.84 mmol) of triethylamine are added successively to a suspension, kept under argon, of 6 mg (0.009 mmol) of bis(triphenylphosphine)palladium dichloride, 3 mg (0.016 mmol) of copper(I) iodide and 178 mg (0.42 mmol) of tert-butyl 3-iodo-5-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate in 2 ml of THF, and the mixture is stirred at room temperature for one hour under argon. Then, for the removal of excess trimethylsilylacetylene, argon is passed through the reaction mixture for 5 minutes. 0.45 ml (0.45 mmol) of a 1 M solution of tetrabutylammonium fluoride in THF are subsequently added, and the reaction mixture is stirred at room temperature for 30 minutes. A solution of 58 mg (0.42 mmol) of benzyl azide in 2 ml of methanol is then added, and the reaction mixture is stirred at room temperature for 48 hours. The reaction mixture is adsorbed onto kieselguhr and chromatographed on a silica-gel column with petroleum ether/ethyl acetate as eluent, giving tert-butyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate as colourless crystals; ESI 456.

Aufarbeitung

  1. customThen, for the removal of excess trimethylsilylacetylene, argon
  2. waitis passed through the reaction mixture for 5 minutes
  3. addition0.45 ml (0.45 mmol) of a 1 M solution of tetrabutylammonium fluoride in THF are subsequently added
  4. stirringthe reaction mixture is stirred at room temperature for 30 minutes
  5. stirringthe reaction mixture is stirred at room temperature for 48 hours
  6. customchromatographed on a silica-gel column with petroleum ether/ethyl acetate as eluent

Quellen und Nachweise

ORD-Eintrag
ord-45aa048f23b84ad886f726280d507db4
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541584B2

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