5-(Tributylstannyl)-1,3-thiazole → 3-Cyclopropyl-3-(4-(7-(thiazol-5-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile

HRID 1853002Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1853002
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH:13]([CH:17]3[CH2:19][CH2:18]3)[CH2:14][C:15]#[N:16])[CH:12]=2)[N:5]2[CH:20]=[CH:21][N:22]=[C:4]2[CH:3]=1.C([Sn](CCCC)(CCCC)[C:28]1[S:32][CH:31]=[N:30][CH:29]=1)CCC.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:17]1([CH:13]([N:11]2[CH:12]=[C:8]([C:6]3[N:5]4[CH:20]=[CH:21][N:22]=[C:4]4[CH:3]=[C:2]([C:28]4[S:32][CH:31]=[N:30][CH:29]=4)[N:7]=3)[CH:9]=[N:10]2)[CH2:14][C:15]#[N:16])[CH2:19][CH2:18]1

Komponenten

5

Edukt 3

HCID 27632575-(Tributylstannyl)-1,3-thiazoleHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 866853033-(4-(7-chloroimidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-3-cyclopropylpropanenitrile

Produkt 1

HCID 674570923-Cyclopropyl-3-(4-(7-(thiazol-5-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrileAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a flask charged with 3-(4-(7-chloroimidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-3-cyclopropylpropanenitrile (Preparation M; 0.020 g, 0.064 mmol), 5-(tributylstannyl)thiazole (0.029 g, 0.077 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.0061 g, 0.013 mmol), and tris(dibenzylideneacetone)dipalladium (0.0059 g, 0.0064 mmol), evacuated and backfilled with argon, was added 1.5 mL of dioxane. Argon was bubbled through the reaction for 5 minutes and the flask was sealed and heated to 100° C. for 3 hours. The reaction mixture was loaded onto a silica gel column pre-wetted and eluted with ethyl acetate containing 0.5% ammonium hydroxide to afford the title compound (0.018 g, 0.050 mmol, 78% yield). MS (apci) m/z=362.1 (M+H).

Aufarbeitung

  1. customevacuated
  2. additionwas added 1.5 mL of dioxane
  3. customArgon was bubbled through the reaction for 5 minutes
  4. customthe flask was sealed
  5. washeluted with ethyl acetate containing 0.5% ammonium hydroxide

Quellen und Nachweise

ORD-Eintrag
ord-0b2e0d27020e47d8a124d17057b2c9d3
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962596B2

Notizen zur Reaktion

Wird geladen…