Methyl 4'-(bromomethyl)biphenyl-2-carboxylate → HCID 22405442, compound

HRID 440836Notes

Reaction equation

HRID 440836 reaction equation
[CH2:1]([C:4]1[NH:8][C:7]2[CH:9]=[C:10]([N:14]3[C:18](=[O:19])[C:17]4=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]4[C:15]3=[O:24])[CH:11]=[C:12]([Cl:13])[C:6]=2[N:5]=1)[CH2:2][CH3:3].CC(C)([O-])C.[K+].Br[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[C:40]([C:45]([O:47][CH3:48])=[O:46])=[CH:41][CH:42]=[CH:43][CH:44]=2)=[CH:35][CH:34]=1>CS(C)=O>[CH2:1]([C:4]1[N:8]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]3[C:40]([C:45]([O:47][CH3:48])=[O:46])=[CH:41][CH:42]=[CH:43][CH:44]=3)=[CH:35][CH:34]=2)[C:7]2[CH:9]=[C:10]([N:14]3[C:18](=[O:19])[C:17]4=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]4[C:15]3=[O:24])[CH:11]=[C:12]([Cl:13])[C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 22075625HCID 22075625, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22405442HCID 22405442, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3.27 g (10.0 mMol) of 2-n-propyl-4-chloro-6-phthalimido-1H-benzimidazole are dissolved in 50 ml of dimethylsulphoxide, 1.23 g (11.0 mMol) of potassium tert.butoxide are added in batches thereto and the resulting mixture is stirred for 30 minutes at ambient temperature. Then 3.38 g (11.0 mMol) of methyl 4'-bromomethyl-biphenyl-2-carboxylate are added in batches thereto. The reaction mixture is then stirred for 3 hours at ambient temperature, stirred into ice water and extracted 3 times with ethyl acetate. The combined organic phases are washed with saline solution and dried over magnesium sulphate. Then the solvent is removed in vacuo and the residue is chromatographed on silica gel (particle size 0.032-0.063 mm), using as eluant first petroleum ether and then mixtures of petroleum ether and ethyl acetate of increasing polarity (9:1, 4:1 and 7:3). The uniform fractions are combined and evaporated down.

Workup

  1. stirringThe reaction mixture is then stirred for 3 hours at ambient temperature
  2. extractionextracted 3 times with ethyl acetate
  3. washThe combined organic phases are washed with saline solution
  4. dry with materialdried over magnesium sulphate
  5. customThen the solvent is removed in vacuo
  6. customthe residue is chromatographed on silica gel (particle size 0.032-0.063 mm)
  7. temperatureof increasing polarity (9:1, 4:1 and 7:3)
  8. customevaporated down

Sources & evidence

ORD record
ord-724bb0f9180446388ba240832e4c48f2
Source dataset
uspto-grants-1996_05
Patent number
US05521177

Reaction notes

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