Dimethylformamide → 3-Chlorothieno(2,3-b)pyridine

HRID 226082

Reaktionsgleichung

Reaktionsgleichung von HRID 226082
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[S:4][CH:3]=1.CN(C=O)C.C(Cl)[Cl:17]>[Cu](Cl)Cl>[Cl:17][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[S:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 2899263-Bromothieno[2,3-b]pyridine

Produkt 1

HCID 5981913-Chlorothieno(2,3-b)pyridineAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24014Cupric ChlorideKatalysator

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

500 mg of 3-Bromo-thieno[2,3-b]pyridine (2.3 mmol) and 136 mg of copper chloride (I) (2.78 mmol) are placed into reaction vial with 3.0 ml of dry DMF. The vial is capped with a Teflon cap and heated at 130° C. overnight. The reaction mixture is poured into CH2Cl2 and washed with NaHCO3, brine and dried over Na2SO4. The solvents are removed and the residue applied onto a chromatography silica-gel column (Hexane:AcOEt=10:1) to give 280 mg of the title compound (71%); mass spectrum (m/e): 170; 1H-NMR (CDCl3): 8.53 (m, 1H), 8.11 (m, 1H), 7.41 (m, 2H) ppm.

Aufarbeitung

  1. customcap
  2. washwashed with NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. customThe solvents are removed

Quellen und Nachweise

ORD-Eintrag
ord-9a16d2eae99c4a91b7f613cb47df8182
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557103B2

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