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Sodium Bicarbonate → HCID 58179870, Verbindung

HRID 1518561
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1518561
FC(F)(F)S(O[C:7]1[CH2:8][CH:9]2[N:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:12]([CH:13]=1)[CH2:11][CH2:10]2)(=O)=O.C([O-])(O)=O.[Na+].[F:29][C:30]1[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:31]=1[N:37]1[C:41]([C:42]2[C:43]([NH2:57])=[N:44][CH:45]=[C:46](B3OC(C)(C)C(C)(C)O3)[CH:47]=2)=[N:40][N:39]=[N:38]1>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:57][C:43]1[N:44]=[CH:45][C:46]([C:7]2[CH2:8][CH:9]3[N:14]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH:12]([CH:13]=2)[CH2:11][CH2:10]3)=[CH:47][C:42]=1[C:41]1[N:37]([C:31]2[CH:32]=[CH:33][CH:34]=[C:35]([F:36])[C:30]=2[F:29])[N:38]=[N:39][N:40]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 226480948-Boc-3-(trifluoromethylsulfonyloxy)-8-azabicyclo[3.2.1]oct-3-eneHCID 581794573-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Produkt 1

HCID 58179870HCID 58179870, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 3-(trifluoromethylsulfonyloxy)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate (50 mg, 140 μmol, 1.0 eq.) in DME (2 mL) was degassed with nitrogen for 15 minutes. NaHCO3 (1.2 mM solution, 350 μL, 420 μmol, 3 eq.) and 3-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (56 mg, 140 μmol, 1.0 eq.) were added and degassing was continued for an additional 30 minutes. PdCl2(dppf)2 (10 mg, 14 μmol, 0.1 eq.) was added and degassing was continued for an additional 15 minutes. The reaction was sealed and microwaved at 90° C. for 15 minutes. After cooling, the organic layer was concentrated, NaHCO3 was added, and the product was extracted with EtOAc. Silica gel chromatography (EtOAc/hexanes) provided tert-butyl 3-(6-amino-5-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-3-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate (34 mg, 51% yield); 1H NMR (300 MHz, CDCl3): 8.25 (m, 1H); 7.6-7.25 (m, 3H); 7.07 (s, 1H); 6.4 (br s, 2H); 6.0 (m, 1H); 4.38 (m, 2H); 2.65 (m, 1H); 2.15 (m, 1H); 2.14-1.5 (m, 4H); 1.44 (s, 9H).

Aufarbeitung

  1. customdegassing
  2. customdegassing
  3. waitwas continued for an additional 15 minutes
  4. customThe reaction was sealed
  5. custommicrowaved at 90° C. for 15 minutes
  6. temperatureAfter cooling
  7. concentrationthe organic layer was concentrated
  8. additionNaHCO3 was added
  9. extractionthe product was extracted with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-2a409b3277de4287b4ce5848027e9268
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08232406B2

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