Diisopropylethylamine → 5-biphenyl-4-yl-6-chloro-2-(methylsulfonyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazole

HRID 1945294Notes

Reaction equation

HRID 1945294 reaction equation
[CH3:1][Si:2]([CH2:5][CH2:6][O:7][CH2:8]Cl)([CH3:4])[CH3:3].[C:10]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:15]=[CH:14][C:13]([C:16]2[C:28]([Cl:29])=[CH:27][C:19]3[NH:20][C:21]([S:23]([CH3:26])(=[O:25])=[O:24])=[N:22][C:18]=3[CH:17]=2)=[CH:12][CH:11]=1.CCN(C(C)C)C(C)C>C1COCC1>[C:10]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:15]=[CH:14][C:13]([C:16]2[C:28]([Cl:29])=[CH:27][C:19]3[N:20]([CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[C:21]([S:23]([CH3:26])(=[O:24])=[O:25])=[N:22][C:18]=3[CH:17]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 684868865-biphenyl-4-yl-6-chloro-2-(methylsulfonyl)-1H-benzimidazole

Product 1

HCID 583871305-biphenyl-4-yl-6-chloro-2-(methylsulfonyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

SEMCl (2.28 mL, 12.87 mmol) was added to a solution of 5-biphenyl-4-yl-6-chloro-2-(methylsulfonyl)-1H-benzimidazole (3.79 g, 9.9 mmol) and Hunig's base (2.08 mL, 11.88 mmol) in THF (20 mL) at 0° C. The reaction was stirred at rt for 3 h then partitioned between EtOAc and saturated aqueous NaHCO3, washed with brine, dried (Na2SO4), filtered and concentrated. Chromatography over silica eluting with 5-25% EtOAc/hexanes afforded the desired product as a white solid.

Workup

  1. customthen partitioned between EtOAc and saturated aqueous NaHCO3
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0686d28ee4194b39b7a0135ebc465a3d
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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