Reaction #156375

Reaction equation

EtOAc

dicyclohexylmethylamine

2H-Indazole-5-carbaldehyde

(2-chloromethoxy-ethyl)-trimethyl-silane

→

title compound

2-(2-Trimethylsilanyl-ethoxymethyl)-2H-indazole-5-carbaldehyde

Solvents

THF

Conditions

Workup

1. 1
   Washwashed successively with 0.5 M aqueous NaOH solution and brine
2. 2
   OtherThe organic layer was dried on Na2SO4
3. 3
   Otherevaporated
4. 4
   Otherthe residue purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, n-hexane/EtOAc=100:0->70:30)

Procedure

2H-Indazole-5-carbaldehyde (Stage 150.5, 770 mg, 5.27 mmol) was dissolved in THF (54 mL) and dicyclohexylmethylamine (1.37 mL, 6.32 mmol) was added. After dropwise addition of (2-chloromethoxy-ethyl)-trimethyl-silane (1.21 mL, 6.32 mmol), the RM was stirred for 48 h at rt. It was then taken into EtOAc and washed successively with 0.5 M aqueous NaOH solution and brine. The organic layer was dried on Na2SO4 and evaporated and the residue purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, n-hexane/EtOAc=100:0->70:30) to afford white crystals of the title compound (tR 7.14 min (conditions 3), MH+=277).

Source