Sodium hydride → Ethyl 4-[3-(2-tert-butoxy-2-oxoethyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]benzoate

HRID 1675775Notes

Reaction equation

HRID 1675775 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)[C:5]2[CH:18]=[CH:19][CH:20]=[CH:21][C:4]=2[NH:3]1.[H-].[Na+].Br[CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27]>CN(C=O)C>[C:29]([O:28][C:26](=[O:27])[CH2:25][N:3]1[C:4]2[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=2[N:6]([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)[C:2]1=[O:1])([CH3:32])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 18449399Ethyl 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)benzoate

Product 1

HCID 18449400Ethyl 4-[3-(2-tert-butoxy-2-oxoethyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ethyl 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)benzoate from Step C (590 mg, 2.09 mmol) in DMF (10 mL) at 0° C. was added sodium hydride (104 mg of a 60% dispersion in mineral oil, 2.60 mmol). The mixture was stirred for 5 min, then tert-butyl bromoacetate (489 mg, 2.51 mmol) was added and stirring was continued for 3 h. The reaction mixture was partitioned between EtOAc (200 mL) and H2O (100 mL). The organic layer was washed with H2O (50 mL), then brine (50 mL), then dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc-100:0 to 0:100, to give the title compound. MS: m/z=397 (M+1).

Workup

  1. stirringstirring
  2. waitwas continued for 3 h
  3. customThe reaction mixture was partitioned between EtOAc (200 mL) and H2O (100 mL)
  4. washThe organic layer was washed with H2O (50 mL)
  5. dry with materialbrine (50 mL), then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-e630cd7ef48943dfa578165adcf226e1
Source dataset
uspto-grants-2011_08
Patent number
US08003792B2

Reaction notes

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