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Sodium Carbonate → tert-butyl 4-(3-(4-aminophenoxy)pyrazin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 473703
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 473703
Cl[C:2]1[C:3]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][N:7]=1.CC1(C)C(C)(C)OB([C:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH:25]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC.O>C(Cl)Cl.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>[NH2:13][C:12]1[CH:14]=[CH:15][C:9]([O:8][C:3]2[C:2]([C:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH:25]=3)=[N:7][CH:6]=[CH:5][N:4]=2)=[CH:10][CH:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 18180031Water 1,2-dimethoxyethaneHCID 201339744-(3-Chloropyrazin-2-yloxy)benzenamine

Produkt 1

HCID 59374116tert-butyl 4-(3-(4-aminophenoxy)pyrazin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Into a sealed 150-mL flask were placed 4-(3-chloropyrazin-2-yloxy)aniline (2 g, 9 mmol) (see Step 1, Example 215), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (4.19 g, 13.5 mmol), trans-dichlorobis-(triphenylphosphine)palladium (II) (0.5 g, 0.72 mmol), sodium carbonate (4.78 g, 45.1 mmol) and 30 mL of 4:1 DME-water. After the mixture was degassed for 5 min, the reaction was stirred at 80° C. for 18 h. The cooled reaction was diluted with CH2Cl2 and washed with aqueous saturated NaHCO3 solution; the aqueous layer was back-extracted with CH2Cl2 (2×). The organic extracts were combined, dried (MgSO4), filtered, and concentrated in vacuo. Flash column chromatography (20% to 60% EtOAc/Hexanes) afforded tert-butyl 4-(3-(4-aminophenoxy)pyrazin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate) as a cream solid. MS (ESI, pos. ion) m/z: 369.0 (M+1).

Aufarbeitung

  1. customInto a sealed 150-mL flask were placed
  2. customAfter the mixture was degassed for 5 min
  3. customThe cooled reaction
  4. washwashed with aqueous saturated NaHCO3 solution
  5. extractionthe aqueous layer was back-extracted with CH2Cl2 (2×)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-622429a4b3ba4b12ae9e5f076aad2b1b
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08637500B2

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