Diisopropylethylamine → HCID 68005840, compound

HRID 74482Notes

Reaction equation

HRID 74482 reaction equation
Cl[CH:2]([O:8][CH3:9])[CH2:3][Si:4]([CH3:7])([CH3:6])[CH3:5].[Br:10][C:11]1[CH:12]=[CH:13][C:14]2[N:18]=[C:17]([CH:19]([F:21])[F:20])[NH:16][C:15]=2[CH:22]=1.C(N(CC)C(C)C)(C)C>ClCCl>[Br:10][C:11]1[CH:12]=[CH:13][C:14]2[N:18]=[C:17]([CH:19]([F:20])[F:21])[N:16]([CH2:9][O:8][CH2:2][CH2:3][Si:4]([CH3:7])([CH3:6])[CH3:5])[C:15]=2[CH:22]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 647235395-bromo-2-(difluoromethyl)-1H-1,3-benzodiazoleHCID 87805942(2-Chloro-methoxy-ethyl)-trimethyl-silane

Product 1

HCID 68005840HCID 68005840, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-Chloro-methoxy-ethyl)-trimethyl-silane (1.1 ml, 6.4 mmol, 1.5 eq.) was added to an anhydrous dichloromethane solution (22 ml) of 6-bromo-2-difluoromethyl-1H-benzimidazol (1.0 g, 4.27 mmol) and N,N-diisopropyl ethyl amine (1.9 ml, 10.6 mmol, 2.5 eq.). This was stirred at room temperature for 18 hours. The reaction mixture was concentrated. The residue obtained by concentration under reduced pressure was purified by silica gel column chromatography. Thus, 6-bromo-2-difluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazole was obtained as a yellow solid (1.37 g, 85%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe residue obtained by concentration under reduced pressure
  3. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-376e286b8d604fb5ad3897ccec8a0208
Source dataset
uspto-grants-2014_09
Patent number
US08829199B2

Reaction notes

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