2-(Methylthio)-4-(tributylstannyl)pyrimidine → 5-Bromo-3-(2-(methylthio)pyrimidin-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

HRID 1529326Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1529326
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[N:6]=[C:5]2I.[CH3:18][S:19][C:20]1[N:25]=[C:24]([Sn](CCCC)(CCCC)CCCC)[CH:23]=[CH:22][N:21]=1>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.[Cu]I.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[N:6]=[C:5]2[C:22]1[CH:23]=[CH:24][N:25]=[C:20]([S:19][CH3:18])[N:21]=1

Komponenten

6

Edukt 2

HCID 27632612-(Methylthio)-4-(tributylstannyl)pyrimidineHCID 679597555-bromo-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Produkt 1

HCID 679597215-Bromo-3-(2-(methylthio)pyrimidin-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazoleAusbeute 42,1 %

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

A glass microwave reaction vessel was charged with 5-bromo-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (2.04 g, 5.01 mmol), Pd(PPh3)4 (0.555 g, 0.480 mmol), CuI (0.130 g, 0.683 mmol) and 2-(methylthio)-4-(tributylstannyl)pyrimidine (2.23 g, 5.37 mmol, Frontier Scientific). DMF (6 mL) was added and the reaction mixture was sealed under argon and heated thermally at 100° C. for 6.5 h. The solvent was removed in vacuo and the residue was dissolved in MeOH, evaporated onto silica gel and purified by flash chromatography (Isco, (80 gram)) eluting with 2M NH3 in MeOH:DCM (0:1→1:19) to give 855 mg of a tan amorphous solid. m/z: 405.0 [M+1].

Aufarbeitung

  1. customA glass microwave reaction vessel
  2. customthe reaction mixture was sealed under argon
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in MeOH
  5. customevaporated onto silica gel
  6. custompurified by flash chromatography (Isco, (80 gram))
  7. washeluting with 2M NH3 in MeOH:DCM (0:1→1:19)

Quellen und Nachweise

ORD-Eintrag
ord-007ea0459bfa49a09fbb377175217bc1
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090593B2

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