Diisopropylethylamine → HCID 68005840, compound

HRID 513868Notes

Reaction equation

HRID 513868 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-1fb922418c6041e684a285a103abca4a
Source dataset
uspto-grants-2015_08
Patent number
US09102692B2

Reaction notes

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