Reaktion #2129718

ord-14c00b20d72142849be11c16b736bad1

Reaktionsgleichung

COc1ccc(-c2n[nH]c(=O)c3ccsc23)cc1
product
COc1ccc(-c2n[nH]c(=O)c3ccsc23)cc1
7-(4-Methoxy-phenyl)-5H-thieno[2,3-d]pyridazin-4-one
O=C([O-])[O-].[Cs+].[Cs+]
Cs2CO3
CC(C)I
2-iodopropane
→
COc1ccc(-c2nn(C(C)C)c(=O)c3ccsc23)cc1
product
Ausbeute 65.0%
COc1ccc(-c2nn(C(C)C)c(=O)c3ccsc23)cc1
5-Isopropyl-7-(4-methoxy-phenyl)-5H-thieno[2,3-d]pyridazin-4-one
Ausbeute 65.0%

Edukte

COc1ccc(-c2n[nH]c(=O)c3ccsc23)cc1
product
COc1ccc(-c2n[nH]c(=O)c3ccsc23)cc1
7-(4-Methoxy-phenyl)-5H-thieno[2,3-d]pyridazin-4-one
O=C([O-])[O-].[Cs+].[Cs+]
Cs2CO3
CC(C)I
2-iodopropane

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
DMF

Reaktionsbedingungen

Temperatur
80°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationfiltered through celite
  2. 2
    Waschenwashed with MeOH:CH2Cl2 (95:5)
  3. 3
    EinengenThe filtrate was concentrated
  4. 4
    Sonstigepurified by silica gel flash chromatography (MeOH:CH2Cl2, 97:3)

Vorschrift

A solution of the product from step 1 in 10 mL of DMF was added Cs2CO3 (2 eq. 1.95 g) and 2-iodopropane (1.2 eq., 360 uL). The reaction was heated to 80° C. for 2 h, and then filtered through celite, washed with MeOH:CH2Cl2 (95:5). The filtrate was concentrated and purified by silica gel flash chromatography (MeOH:CH2Cl2, 97:3) to afford 585 mg (65%) of the product: Mp 124-6° C.; MS m/z 301 (M+H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08586588B2uspto-grants-2013_11