Methyl iodide → 2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole

HRID 2353160Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2353160
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[N:12][NH:13]3)[O:3]1.[H-].[Na+].I[CH3:22]>CN(C=O)C.C1COCC1.C(Cl)Cl>[CH3:22][N:13]1[C:14]2[C:10](=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:18])([CH3:1])[O:3]3)[CH:17]=[CH:16][CH:15]=2)[CH:11]=[N:12]1.[CH3:22][N:12]1[CH:11]=[C:10]2[C:14]([CH:15]=[CH:16][CH:17]=[C:9]2[B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:18])([CH3:1])[O:3]2)=[N:13]1

Komponenten

8

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole

Produkt 2

HCID 441182542-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazoleHCID 454801871-Methyl-1H-indazole-4-boronic acid pinacol ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indazole (400 mg) in dry DMF (4 mL) precooled to 0° C. was added to a suspension of sodium hydride (80 mg) in dry THF (5 mL) at −78° C. under inert atmosphere. After 30 min, iodomethane (112 uL) was added to the mixture at −78° C. The reaction mixture was allowed slowly to warm up to room temperature overnight and then diluted with DCM, washed with brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified using flash chromatography to yield 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indazole (143 mg) and 2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2H-indazole (160 mg).

Aufarbeitung

  1. customprecooled to 0° C.
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-77ae0d3b29fc4982b73e4c2cec792cb0
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07750002B2

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