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Sodium Bicarbonate → HCID 58179868, Verbindung

HRID 254009
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 254009
CC1(C)C(C)(C)OB([C:9]2[CH2:10][CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH:15]=2)O1.C([O-])(O)=O.[Na+].Br[C:30]1[CH:31]=[C:32]([C:37]2[N:41]([C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[C:43]=3[F:49])[N:40]=[N:39][N:38]=2)[C:33]([NH2:36])=[N:34][CH:35]=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]>[NH2:36][C:33]1[N:34]=[CH:35][C:30]([C:9]2[CH2:10][CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:14][CH:15]=2)=[CH:31][C:32]=1[C:37]1[N:41]([C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[C:43]=2[F:49])[N:40]=[N:39][N:38]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 247624635-bromo-3-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amineHCID 581796955-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 58179868HCID 58179868, VerbindungAusbeute 58,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

(Z)-tert-Butyl 3,4-dihydro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-azepine-1(7H)-carboxylate (510 mg, 1.44 mmol, 1.1 eq.) was dissolved in DME (14 mL) and degassed with nitrogen for 15 minutes. NaHCO3 (1.2 M solution, 3.25 mL, 3.9 mmol, 3 eq.) and 5-bromo-3-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine (420 mg, 1.3 mmol, 1 eq.) were added and the mixture degassed with nitrogen for an additional 30 minutes. PdCl2(dppf)2 (95 mg, 0.13 mmol, 0.1 eq.) was added and the mixture degassed with nitrogen for an additional 15 minutes. The reaction was microwaved in a sealed tube for 20 min at 90° C. To drive the reaction to completion, additional PdCl2(dppf)2 (95 mg, 0.13 mmol, 0.1 eq.) was added under an atmosphere of nitrogen and the reaction microwaved for an additional 20 min at 90° C. The mixture was concentrated, NaHCO3 was added, and the product was extracted with ethyl acetate. The organics were filtered through floricil and purified by silica gel chromatography (EtOAc/hexanes) to provide (E)-tert-butyl 5-(6-amino-5-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-3-yl)-3,4-dihydro-2H-azepine-1(7H)-carboxylate (360 mg, 0.76 mmol, 53% yield); 1H NMR (300 MHz, CDCl3): 8.2 (m, 1H); 7.5 (m, 1H); 7.45-7.3 (m, 2H); 7.02 (s, 1H); 6.4 (br s, 2H); 5.6 (m, 1H); 3.8 (m, 2H); 3.55 (m, 2H); 2.2 (m, 2H); 1.7 (m, 2H) 1.45 (s, 9H).

Aufarbeitung

  1. customdegassed with nitrogen for 15 minutes
  2. customthe mixture degassed with nitrogen for an additional 30 minutes
  3. customthe mixture degassed with nitrogen for an additional 15 minutes
  4. customThe reaction was microwaved in a sealed tube for 20 min at 90° C
  5. additionwas added under an atmosphere of nitrogen
  6. customthe reaction microwaved for an additional 20 min at 90° C
  7. concentrationThe mixture was concentrated
  8. additionNaHCO3 was added
  9. extractionthe product was extracted with ethyl acetate
  10. filtrationThe organics were filtered through floricil
  11. custompurified by silica gel chromatography (EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3e4aac78b59e41b582dec568265e8d95
Quelldatensatz
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07872031B2

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