1,3-Propanediol → HCID 11153793, compound

HRID 644506Notes

Reaction equation

HRID 644506 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:20]=[C:19](I)[C:9]2[N:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:11]=[N:12][C:8]=2[CH:7]=1)=[O:5])[CH3:2].[C:22]([NH:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1)(=[O:24])[CH3:23].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>[C:22]([NH:25][C:26]1[CH:31]=[C:30]([C:19]2[C:9]3[N:10]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:11]=[N:12][C:8]=3[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:20]=2)[CH:29]=[CH:28][CH:27]=1)(=[O:24])[CH3:23]

Participants

8

Reactant 4

HCID 104421,3-PropanediolHCID 11430Potassium CarbonateHCID 157274(3-Acetamidophenyl)boronic acidHCID 67485000HCID 67485000, compound

Product 1

HCID 11153793HCID 11153793, compound

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 5-ethoxycarbonyl-7-iodo-1-phenylbenzimidazole (0.70 g, 1.8 mmol), 3-acetamidophenylboronic acid (0.48 g, 2.7 mmol), 1,3-propanediol (0.65 ml, 8.9 mmol), potassium carbonate (1.23 g, 8.9 mmol) and bis(triphenylphosphin)palladium dichloride (50 mg, 0.07 mmol) in a mixture of dimethoxyethane (10 ml) and water (5 ml) was stirred at reflux for 1 hour. The cooled reaction mixture was concentrated under reduced pressure, and the concentrate was partitioned between water and ethyl acetate. The organic phase was dried and concentrated under reduced pressure, and the concentrate was triturated in ethyl acetate leaving the product as an off-white solid (0.48 g, 67%) m/z, 400.2 (M+H)+.

Workup

  1. temperatureat reflux for 1 hour
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. customthe concentrate was partitioned between water and ethyl acetate
  5. customThe organic phase was dried
  6. concentrationconcentrated under reduced pressure
  7. customthe concentrate was triturated in ethyl acetate leaving the product as an off-white solid (0.48 g, 67%) m/z, 400.2 (M+H)+

Sources & evidence

ORD record
ord-936a8dcdaea648a9b4cf85ab86b66eae
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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