Imidazole → Ethyl 6-(((triisopropylsilyl)oxy)methyl)imidazo[1,2-a]pyridine-3-carboxylate

HRID 405805Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405805
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][N:11]=2)[CH:8]=1.N1C=CN=C1.[CH3:22][CH:23]([Si:25](Cl)([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[CH3:24]>CN(C1C=CN=CC=1)C.ClCCl>[CH:23]([Si:25]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[O:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][N:11]=2)[CH:8]=1)([CH3:24])[CH3:22]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 19701440Ethyl 6-(hydroxymethyl)imidazo[1,2-a]pyridine-3-carboxylate

Produkt 1

HCID 71281302Ethyl 6-(((triisopropylsilyl)oxy)methyl)imidazo[1,2-a]pyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of ethyl 6-(hydroxymethyl)imidazo[1,2-a]pyridine-3-carboxylate (59) (497.0 mg, 2.26 mmol), DMAP (12.2 mg, 0.1 mmol) and 1H-imidazole (154.0 mg, 2.26 mmol) in dichloromethane (10 mL), was added TIPSCl (523.0 mg, 2.71 mmol). The resulting mixture was stirred overnight at room temperature. The solvent was removed under vacuum to yield crude ethyl 6-(((triisopropylsilyl)oxy)methyl)imidazo[1,2-a]pyridine-3-carboxylate (60). MS m/z 377.2 (M+1)+.

Aufarbeitung

  1. customThe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-16f6e7ed87b84991a47c1885c5e06b38
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754071B2

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