Triethylamine → HCID 11256556, compound

HRID 1661892Notes

Reaction equation

HRID 1661892 reaction equation
I[C:2]1[C:10]2[N:9]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=3)[N:7]([CH2:20][CH2:21][O:22][CH3:23])[C:6]=2[C:5]([O:24][CH3:25])=[CH:4][CH:3]=1.[CH2:26](N(CC)CC)[CH3:27].C([Si](C)(C)C)#C>C(#N)C.CC(O)=O.CC(O)=O.[Pd]>[C:26]([C:2]1[C:10]2[N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:15][CH:16]=3)[N:7]([CH2:20][CH2:21][O:22][CH3:23])[C:6]=2[C:5]([O:24][CH3:25])=[CH:4][CH:3]=1)#[CH:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 114423054-Iodo-7-methoxy-1-(2-methoxyethyl)-2-[4-(1-methylethyl)phenyl]-1H-benzimidazole

Product 1

HCID 11256556HCID 11256556, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 4144353Palladium (II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 50 mg (0.111 mmol) 4-iodo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole, 0.1 ml (0.77 mmol) triethylamine, 0.1 ml (0.7 mmol) ethinyltrimethylsilane and 5 mg palladium-II-acetate in 1 ml acetonitrile is stirred at 50° C. for 3 hours. Then the reaction mixture is cooled to room temperature and poured on water and extracted (3×) with ethyl acetate. The combined organic layers are washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1) to afford 17 mg of the title compound as colorless oil.

Workup

  1. temperatureThen the reaction mixture is cooled to room temperature
  2. additionpoured on water
  3. extractionextracted (3×) with ethyl acetate
  4. washThe combined organic layers are washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1)

Sources & evidence

ORD record
ord-618d08272f724907b63460454d7a97c1
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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