Cesium carbonate → methyl 1-[(7-cyano-2-naphthyl)methyl]-2-oxo-(3H)-benzimidazole-5-carboxylate

HRID 1861865Notes

Reaction equation

HRID 1861865 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:10][C:4]=2[N:3]1C(OCC1C=CC=CC=1)=O.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:32][C:33]1[CH:42]=[C:41]2[C:36]([CH:37]=[CH:38][C:39]([C:43]#[N:44])=[CH:40]2)=[CH:35][CH:34]=1>CN(C=O)C.C(OCC)(=O)C>[C:43]([C:39]1[CH:40]=[C:41]2[C:36]([CH:35]=[CH:34][C:33]([CH2:32][N:6]3[C:5]4[CH:7]=[CH:8][C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:10][C:4]=4[NH:3][C:2]3=[O:1])=[CH:42]2)=[CH:37][CH:38]=1)#[N:44]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 98377487-(Bromomethyl)-2-naphthonitrileHCID 186216456-Methyl 1-(phenylmethyl) 2,3-dihydro-2-oxo-1H-benzimidazole-1,6-dicarboxylate

Product 1

HCID 18621644methyl 1-[(7-cyano-2-naphthyl)methyl]-2-oxo-(3H)-benzimidazole-5-carboxylateYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a chilled solution of methyl 2-oxo-3-(benzyloxycarbonyl)—(3H)—benzimidazole-5-carboxylate (110 mg, 0.337 mmol) in DMF (3 mL) was added cesium carbonate (0.275 g, 0.84 mmol) followed by 7-(bromomethyl)naphthalene-2-carbonitrile (108 mg, 0.44 mmol). The reaction was stirred at room temperature for 1.5 hours, diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate and concentrated in vacuo. This residue was redissolved in methanol (4 mL), CH3CN (3 mL) and IN LiOH (0.7 mL). The reaction mixture was stirred for 1 hour, acidified with 1N HCl (0.7 mL), filtered and dried to yield methyl 1-[(7-cyano(2-naphthyl))methyl]-2-oxo-(3H)—benzimidazole-5-carboxylate (84 mg, 70%) as awhite solid. ES-MS (M+H)+=358.1.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. dissolutionThis residue was redissolved in methanol (4 mL)
  5. stirringThe reaction mixture was stirred for 1 hour
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-6caf8dee3e3743d48ba07a3618231ecc
Source dataset
uspto-grants-2003_03
Patent number
US06534535B1

Reaction notes

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