Triethylamine → N-tert-butyl-2-(5-((6-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

HRID 29113

Reaktionsgleichung

Reaktionsgleichung von HRID 29113
[C:1]([NH:5][C:6]1[N:10]2[CH:11]=[CH:12][N:13]=[CH:14][C:9]2=[N:8][C:7]=1[C:15]1[S:16][C:17]([C:20]#[CH:21])=[CH:18][CH:19]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[N:24]=1.CCN(CC)CC.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CC(=O)OCC.[Cu]I.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>[C:1]([NH:5][C:6]1[N:10]2[CH:11]=[CH:12][N:13]=[CH:14][C:9]2=[N:8][C:7]=1[C:15]1[S:16][C:17]([C:20]#[C:21][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[N:24]=2)=[CH:18][CH:19]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 6394382-Bromo-6-fluoropyridineHCID 86613493Tert-butyl-[2-(5-ethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

Produkt 1

HCID 11552894N-tert-butyl-2-(5-((6-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amineAusbeute 30,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

500 mg (1.69 mmol) of tert-butyl-[2-(5-ethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine (synthesis described in Example 158 part b) were dissolved together with 355 mg (2.02 mmol) of 2-bromo-6-fluoro-pyridine in DMF (20 ml). 2.4 ml (16.9 mmol) of NEt3, 32 mg (0.17 mmol) of copper(I) iodide and 119 mg (0.17 mmol) bis(triphenylphosphine)-palladium(II) chloride were added to this solution. The reaction mixture was heated to 50° C. for 6 h. The mixture was then diluted with EA and combined with a 1M aq. Na2CO3 solution. The phases were separated and the aq. phase was extracted with EA. The combined organic phases were washed with a 1M aq. Na2CO3 solution, dried over MgSO4, filtered and evaporated under a vacuum. 200 mg (0.51 mmol, 30%) of N-tert-butyl-2-(5-((6-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine were obtained by CC (EA) of the group.

Aufarbeitung

  1. customThe phases were separated
  2. extractionthe aq. phase was extracted with EA
  3. washThe combined organic phases were washed with a 1M aq. Na2CO3 solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9eda6fc09d7f4466ab4ac41a09e23be2
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420056B2

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