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7-Chlorothieno[3,2-b]pyridine → HCID 66599084, Verbindung

HRID 1475578
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1475578
[Cl:1][C:2]1[CH:7]=[CH:6]N=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12.[Li][CH2:12]CCC.C(OC(=O)[N:22]([CH2:27][C:28]1[CH:29]=[N:30][C:31](Br)=[CH:32][CH:33]=1)[CH2:23][CH2:24][O:25][CH3:26])(C)(C)C>C1COCC1.[Cl-].[Cl-].[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[C:3]2[S:10][C:9]([C:31]3[N:30]=[CH:29][C:28]([CH2:27][NH:22][CH2:23][CH2:24][O:25][CH3:26])=[CH:33][CH:32]=3)=[CH:8][C:4]=2[CH:12]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 112752517-Chlorothieno[3,2-b]pyridineHCID 57919609tert-Butyl [(6-Bromopyridin-3-yl)methyl](2-methoxyethyl)carbamateHCID 178418339Butyllithium

Produkt 1

HCID 66599084HCID 66599084, VerbindungAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysator
HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 7-chlorothieno[3,2-b]pyridine 6 (7.37 g, 43.4 mmol, 1.5 eq) in THF (70 mL) at −10° C. in a 250 mL round-bottom flask was added n-BuLi (17.38 mL, 43.4 mmol, 1.5 eq). After 1 h, ZnCl2 (1M in ether) (43.4 mL, 43.4 mmol, 1.5 eq) was added at −10° C. and the reaction mixture was allowed to warm up to r.t. After 1 h, Pd(PPh3)4 (0.669 g, 0.579 mmol, 0.02 eq) and bromide 10 (10 g, 29 mmol, 1 eq) in THF (10.5 mL) were added and the mixture was heated to reflux for 1 h. After cooling to room temperature the reaction mixture was concentrated to dryness. DCM (200 mL)/water (160 mL)/NH4OH (40 mL) were added to the solid and the resultant mixture (an emulsion) was stirred for 1 h. Brine (50 ml) was added to the emulsion and the stirring was continued for an additional 10 min. The mixture was then filtered through a paper filter and phases were separated. The aqueous phase was extracted with DCM (2×50 mL). The organic phases were combined, dried over Na2SO4 and concentrated to dryness. MTBE (30 mL) was added to the solid and the suspension was stirred for 30 min. The solid was collected by filtration, washed with MTBE (2×5 mL) and dried to afford of 11 as a beige solid (8.02 g, 64% yield). MS (m/z): 434.2 (M+1).

Aufarbeitung

  1. waitAfter 1 h
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 1 h
  4. temperatureAfter cooling to room temperature the reaction mixture
  5. concentrationwas concentrated to dryness
  6. additionDCM (200 mL)/water (160 mL)/NH4OH (40 mL) were added to the solid
  7. additionBrine (50 ml) was added to the emulsion
  8. waitthe stirring was continued for an additional 10 min
  9. filtrationThe mixture was then filtered through a paper
  10. filtrationfilter
  11. customphases were separated
  12. extractionThe aqueous phase was extracted with DCM (2×50 mL)
  13. dry with materialdried over Na2SO4
  14. concentrationconcentrated to dryness
  15. additionMTBE (30 mL) was added to the solid
  16. stirringthe suspension was stirred for 30 min
  17. filtrationThe solid was collected by filtration
  18. washwashed with MTBE (2×5 mL)
  19. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7ec8cab0652b42a08cff89e1e4614935
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09018378B2

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