1,3-Propanediol → HCID 11174830, compound

HRID 644539Notes

Reaction equation

HRID 644539 reaction equation
I[C:2]1[C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1.[O:21]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22]1.C(O)CCO.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:21]1[CH:25]=[CH:24][C:23]([C:2]2[C:7]3[N:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH:9]=[N:10][C:6]=3[CH:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=2)=[CH:22]1

Participants

8

Reactant 4

HCID 104421,3-PropanediolHCID 11430Potassium CarbonateHCID 2734358Furan-3-boronic acidHCID 194260247-Iodo-1-phenyl-5-(trifluoromethyl)-1H-benzimidazole

Product 1

HCID 11174830HCID 11174830, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 7-iodo-1-phenyl-5-trifluoromethylbenzimidazole (0.5 g, 1.25 mmol), 3-furane boronic acid (0.2 g, 1.87 mmol), 1,3-propanediol (0.45 ml, 6.2 mmol), potassium carbonate (0.86 g, 6.2 mmol) and bis(triphenylphosphin)palladium dichloride (50 mg, 0.07 mmol) in a mixture of dimethoxyethane (10 ml) and water (15 ml) was stirred at reflux in a nitrogen atmosphere for 30 min. The cooled reaction mixture was partitioned between ethyl acetate and water and the organic layer was dried over magnesium sulphate and evaporated under reduced pressure. The residue was triturated in diethyl ether to afford the title product as an off-white solid (0.22 g, 54%) m/z, 329.1 (M+H)+.

Workup

  1. temperatureat reflux in a nitrogen atmosphere for 30 min
  2. customThe cooled reaction mixture
  3. customwas partitioned between ethyl acetate and water
  4. dry with materialthe organic layer was dried over magnesium sulphate
  5. customevaporated under reduced pressure
  6. customThe residue was triturated in diethyl ether

Sources & evidence

ORD record
ord-d9a2064a6c55480985e05b884ac7efcb
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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