N-Methyl dicyclohexylamine → 5-bromo-7-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole

HRID 469305Notes

Reaction equation

HRID 469305 reaction equation
Cl[CH2:2][O:3][CH2:4][CH2:5][Si:6]([CH3:9])([CH3:8])[CH3:7].[Br:10][C:11]1[CH:12]=[C:13]2[C:17](=[C:18]([CH3:20])[CH:19]=1)[NH:16][N:15]=[CH:14]2.CN(C1CCCCC1)C1CCCCC1>C1COCC1>[Br:10][C:11]1[CH:12]=[C:13]2[C:17](=[C:18]([CH3:20])[CH:19]=1)[N:16]([CH2:2][O:3][CH2:4][CH2:5][Si:6]([CH3:9])([CH3:8])[CH3:7])[N:15]=[CH:14]2

Participants

5

Reactant 3

HCID 24210N-Methyl dicyclohexylamineHCID 13820335-Bromo-7-methyl-1H-indazoleHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 581812085-bromo-7-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.95 mL (11.0 mmol) (2-chloromethoxy-ethyl)-trimethyl-silane were added to 2.11 g (10.0 mmol) 5-bromo-7-methyl-1H-indazole and 1.80 mL (12.3 mmol) N-methyldicyclohexylamine in 50 mL THF and stirred overnight at RT. The precipitate formed was filtered off and the filtrate was evaporated down. The residue was purified by flash chromatography.

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered off
  3. customthe filtrate was evaporated down
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-bb0ef38bd3d1402b842c1a6df6a14b57
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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