Reaktion #166496

ord-775cfd77318c437fa01462f6fcd3da16

Reaktionsgleichung

CCc1nn(Cc2cn[nH]c2)c2cccc(NC(=O)c3cnc4ccccn34)c12
N-(1-((1H-pyrazol-4-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide
CC(C)(C)[Si](C)(C)OCCBr
(2-bromoethoxy)(tert-butyl)dimethylsilane
O.[Cs+].[OH-]
cesium hydroxide hydrate
CCc1nn(Cc2cnn(CCO[Si](C)(C)C(C)(C)C)c2)c2cccc(NC(=O)c3cnc4ccccn34)c12
desired product
Ausbeute 56.6%
CCc1nn(Cc2cnn(CCO[Si](C)(C)C(C)(C)C)c2)c2cccc(NC(=O)c3cnc4ccccn34)c12
N-(1-((1-(2-(tert-butyldimethylsilyloxy)ethyl)-1H-pyrazol-4-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide
Ausbeute 56.6%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Einengenconcentrated
  2. 2
    SonstigePurification by silica gel chromatography (DCM/MeOH 10:1)

Vorschrift

To N-(1-((1H-pyrazol-4-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (20 mg, 0.052 mmol) in DMF (5 mL) was added (2-bromoethoxy)(tert-butyl)dimethylsilane (37 mg, 0.16 mmol), cesium hydroxide hydrate (17 mg, 0.10 mmol) and 4 angstrom molecular sieves (2 g). The reaction mixture was stirred for 3 hours and then concentrated. Purification by silica gel chromatography (DCM/MeOH 10:1) gave the desired product (16 mg).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08841455B2uspto-grants-2014_09