2-Chloro-4-(tributylstannyl)pyrimidine → 3-(2-chloropyrimidin-4-yl)-N,N-dimethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxamide

HRID 1529444Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1529444
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH:9]=2)[N:4]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[N:3]=1.[Cl:22][C:23]1[N:28]=[C:27]([Sn](CCCC)(CCCC)CCCC)[CH:26]=[CH:25][N:24]=1>CN(C=O)C.[Cu]I.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:22][C:23]1[N:28]=[C:27]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH:9]=3)[N:4]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[N:3]=2)[CH:26]=[CH:25][N:24]=1

Komponenten

6

Edukt 2

HCID 468399532-Chloro-4-(tributylstannyl)pyrimidineHCID 679599763-iodo-N,N-dimethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxamide

Produkt 1

HCID 867097953-(2-chloropyrimidin-4-yl)-N,N-dimethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxamideAusbeute 103,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 3-iodo-N,N-dimethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxamide (3 g, 7.53 mmol) and 2-chloro-4-(tributylstannyl)pyrimidine (3.6 g, 8.04 mmol) in DMF (35 mL) under argon atmosphere was added CuI (1.7 g, 9.02 mmol) and Pd(PPh3)4 (868.5 mg, 0.75 mmol) and argon gas was bubbled for 15 min. The reaction was heated at 100° C. for 1 h. The reaction was quenched with water to give off white precipitate. The suspension filtered, washed with water and dried. The crude was purified by neutral alumina column chromatography (eluting with 100% EtOAc) to give 3-(2-chloropyrimidin-4-yl)-N,N-dimethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxamide (3.0 g, 58%) as an off white solid. MS (ESI, pos. ion) m/z: 386.2 (M+1).

Aufarbeitung

  1. customwas bubbled for 15 min
  2. customThe reaction was quenched with water
  3. customto give off white precipitate
  4. filtrationThe suspension filtered
  5. washwashed with water
  6. customdried
  7. customThe crude was purified by neutral alumina column chromatography (eluting with 100% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-26e7c3d818504ca88461cb725db222b8
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090593B2

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