Nitrogen → 1-(6-Bromo-4-(pyridin-2-yl)thiazolo[5,4-c]pyridin-2-yl)-3-ethylurea

HRID 712314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 712314
Br[C:2]1[C:7]2[S:8][C:9]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:10][C:6]=2[CH:5]=[C:4]([Br:17])[N:3]=1.C([Sn](CCCC)(CCCC)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)CCC.N#N>CN(C=O)C.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>[Br:17][C:4]1[N:3]=[C:2]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:7]2[S:8][C:9]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:10][C:6]=2[CH:5]=1

Komponenten

6

Edukt 3

HCID 947NitrogenHCID 6077842-(Tributylstannyl)pyridineHCID 580332371-(4,6-Dibromothiazolo[5,4-c]pyridin-2-yl)-3-ethylurea2×

Produkt 1

HCID 866640261-(6-Bromo-4-(pyridin-2-yl)thiazolo[5,4-c]pyridin-2-yl)-3-ethylurea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 1-(4,6-dibromothiazolo[5,4-c]pyridin-2-yl)-3-ethylurea (Intermediate 8) (0.25 g, 0.65 mmol) and 2-(tributylstannyl)pyridine (0.21 mL, 0.65 mmol) in DMF (10 mL) was purged with N2 for 15 min followed by addition of tetrakis(triphenylphosphine)palladium (0) (0.075 g, 0.065 mmol). The reaction mixture was again degassed by purging N2 for 15 min then heated to 80° C. for 16 h. The solvent was distilled under reduced pressure, water (25 mL) added and extracted with EtOAc (3×100 mL). The combined organics were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified over silica gel (100-200M, 2.50% MeOH-DCM) to afford the desired product that was finally triturated with ether (0.10 g, 40%). The regio chemistry was ascertained by NOE experiments.

Aufarbeitung

  1. customThe reaction mixture was again degassed
  2. customby purging N2 for 15 min
  3. distillationThe solvent was distilled under reduced pressure, water (25 mL)
  4. additionadded
  5. extractionextracted with EtOAc (3×100 mL)
  6. dry with materialThe combined organics were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified over silica gel (100-200M, 2.50% MeOH-DCM)

Quellen und Nachweise

ORD-Eintrag
ord-427a4618b4174d189d8dda0a636d29c6
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181234B2

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