4-Chloro-2-(tributylstannyl)pyrimidine → 5-(3-(4-chloropyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine

HRID 634244Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 634244
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[O:15][C:14]([NH:16][CH:17]([CH3:19])[CH3:18])=[N:13][N:12]=3)[CH:9]=2)[N:4]([S:20]([C:23]2[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH:3]=1.[Cl:30][C:31]1[CH:36]=[CH:35][N:34]=[C:33]([Sn](CCCC)(CCCC)CCCC)[N:32]=1>CN(C=O)C.C(Cl)Cl.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:30][C:31]1[CH:36]=[CH:35][N:34]=[C:33]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]4[O:15][C:14]([NH:16][CH:17]([CH3:18])[CH3:19])=[N:13][N:12]=4)[CH:9]=3)[N:4]([S:20]([C:23]3[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:3]=2)[N:32]=1

Komponenten

6

Edukt 2

HCID 149763044-Chloro-2-(tributylstannyl)pyrimidineHCID 683289275-(3-iodo-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine

Produkt 1

HCID 867251125-(3-(4-chloropyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amineAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A glass microwave reaction vessel was charged with 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (1.00 g, 1.914 mmol) and 4-chloro-2-(tributylstannyl)pyrimidine (0.966 g, 2.393 mmol) in DMF (5 mL) followed by Pd(PPh3)4 (0.111 g, 0.096 mmol, Strem) and Cut (0.072 g, 0.383 mmol, Aldrich). The reaction was stirred and heated in a Initiator microwave reactor at 100° C. for 1 h. The mixture was then diluted with DCM and washed with H2O, brine. The organic layer was dried (MgSO4), filtered and concentrated. The residue was purified with flash chromatography (eluent: 25%-60% EtOAc in Hexanes) to give 5-(3-(4-chloropyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (550 mg, 1.081 mmol, 56.4%) as a green solid. MS (ESI, pos. ion) m/z: 508.9 (M+1).

Aufarbeitung

  1. customA glass microwave reaction vessel
  2. washwashed with H2O, brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with flash chromatography (eluent: 25%-60% EtOAc in Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ee5b6ea7020d46b6bca67e88433a3297
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321756B2

Notizen zur Reaktion

Wird geladen…