tert-Butanol → HCID 67360378, compound

HRID 1747475Notes

Reaction equation

HRID 1747475 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:15][C:16]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]3[C:17]=2[CH:18]=[CH:19][NH:20]3)[C:7]1=[O:26].C([OH:32])(C)(C)C>[Zn]>[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:15][C:16]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]3[C:17]=2[CH2:18][C:19](=[O:32])[NH:20]3)[C:7]1=[O:26]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 67361638HCID 67361638, compound

Product 1

HCID 67360378HCID 67360378, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

3-[3-(6-Chloro-1H-indol-4-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-propionic acid methyl ester (248 mg, 0.64 mmol) is dissolved it tert-butanol (20 mL) at 40° C. The reaction is stirred and pyridiniumtrbromide is added portion wise over 5 minutes. The reaction is stirred for 10 minutes and concentrated in vacuo. The crude material is dissolved in acetic acid (10 mL) and zinc powder (211 mg, 3.2 mmol)is added to the reaction. The reaction is stirred at room temperature for one hour, then the solvent evaporated in vacuo. The residue is taken up in dimethyl sulfoxide and filtered. The crude material is purified by preparative reverse phase LC to give the title compound (34 mg 0.09 mmol, 36%).

Workup

  1. additionpyridiniumtrbromide is added portion wise over 5 minutes
  2. stirringThe reaction is stirred for 10 minutes
  3. concentrationconcentrated in vacuo
  4. dissolutionThe crude material is dissolved in acetic acid (10 mL)
  5. stirringThe reaction is stirred at room temperature for one hour
  6. customthe solvent evaporated in vacuo
  7. filtrationfiltered
  8. customThe crude material is purified by preparative reverse phase LC

Sources & evidence

ORD record
ord-2874c84eeabf4447a908dee6f6c191d3
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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