Acetic Acid → 1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole

HRID 1862165Notes

Reaction equation

HRID 1862165 reaction equation
N1C=CC([C:7]2[CH:15]=[C:14]3[C:10]([C:11](C=O)=[N:12][N:13]3[CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])=[CH:9][CH:8]=2)=CC=1.NN1C=CC=C1.C(O)(=O)C>C(O)C>[CH3:21][Si:20]([CH3:23])([CH3:22])[CH2:19][CH2:18][O:17][CH2:16][N:13]1[C:14]2[C:10](=[CH:9][CH:8]=[CH:7][CH:15]=2)[CH:11]=[N:12]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1365891-AminopyrroleHCID 21877293HCID 21877293, compound

Product 1

HCID 116874401-(2-trimethylsilanyl-ethoxymethyl)-1H-indazoleYield 95.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-pyridin-4-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole-3-carbaldehyde (208 mg, 0.59 mmol), N-aminopyrrole (145 mg, 1.76 mmol), and acetic acid (5.8 μl) in ethanol (1 ml) was held at 95° C. for 16 h. The solution was then evaporated under reduced pressure, and purified by silica gel chromatography to give 6-pyrid-4-yl-3-E-N-(pyrrol-1-yl)iminomethyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole as an oil (140 mg, 57%). 1H NMR (300 MHz, CDCl3) δ 9.08 (s, 1H), 8.71 (d, 2H, J=6.1 Hz), 8.46 (d, 1H, J=8.5 Hz), 8.34 (s, 1H), 7.85 (d, 2H, J=6.2 Hz), 7.80 (d, 1H, J=8.5 Hz), 7.56 (t, 2H, J=2.3 Hz), 6.25 (t, 2H, J=2.3 Hz), 5.93 (s, 1H), 5.74 (s, 2H), 3.64 (t, 2H, J=7.9 Hz), 0.86 (t, 2H, J=7.9 Hz), 0.00 (s, 9H).

Workup

  1. customThe solution was then evaporated under reduced pressure
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-cda3bf012c38493aac33bc66c7d9e7d6
Source dataset
uspto-grants-2003_03
Patent number
US06534524B1

Reaction notes

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