Sodium hydride → 2-{4-[6-chloro-2-ethyl-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethyl 3-pyridinylsulfonylcarbamate

HRID 858486Notes

Reaction equation

HRID 858486 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([NH2:10])(=[O:9])=[O:8])[CH:2]=1.[H-].[Na+].[C:13](=O)([O:39]C1C=CC=CC=1)[O:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:27]3[CH:28]=[C:29]([Cl:36])[C:30]([C:32]([F:35])([F:34])[F:33])=[CH:31][C:26]=3[N:25]=[C:24]2[CH2:37][CH3:38])=[CH:19][CH:18]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:36][C:29]1[C:30]([C:32]([F:34])([F:33])[F:35])=[CH:31][C:26]2[N:25]=[C:24]([CH2:37][CH3:38])[N:23]([C:20]3[CH:19]=[CH:18][C:17]([CH2:16][CH2:15][O:14][C:13](=[O:39])[NH:10][S:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)(=[O:9])=[O:8])=[CH:22][CH:21]=3)[C:27]=2[CH:28]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 232710pyridine-3-sulfonamideHCID 218764092-{4-[6-chloro-2-ethyl-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethyl phenyl carbonate

Product 1

HCID 218758962-{4-[6-chloro-2-ethyl-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethyl 3-pyridinylsulfonylcarbamateYield 19%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 3-pyridinesulfonamide (Rafik, Karaman; et al., J. Am. Chem. Soc., 1992, 114, 4889, 120 mg, 0.76 mmol) in DMF (3 mL) was added NaH (60% oil dispersion, 27 mg, 0.68 mmol) at room temperature. After 10 min., phenyl 2-[4-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl]ethylcarbamate (step 1, 313 mg, 0.64 mmol) was added, and the mixture was stirred for 9 h at 80° C. The mixture was diluted with ethyl acetate (50 mL), and washed with water and brine. The organic layer was dried (Na2SO4) and concentrated. Purification by TLC developing with dichloromethane/methanol (6:1) and TLC developing with dichloromethane/methanol (10:1) gave 67 mg (19%) of the title compound as colorless solid.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification by TLC

Sources & evidence

ORD record
ord-2e69983740f04667be7475a66642590a
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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