1,3-Propanediol → HCID 67484042, compound

HRID 2262735Notes

Reaction equation

HRID 2262735 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([CH2:17][N:18]4[C:26](=[O:27])[C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[C:19]4=[O:28])=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.[N:29]1[CH:34]=[CH:33][CH:32]=[C:31](B(O)O)[CH:30]=1.C(=O)([O-])[O-].[K+].[K+].C(O)CCO>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>[N:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:2]2[CH:3]=[C:4]([N:8]3[C:12]4[CH:13]=[CH:14][C:15]([CH2:17][N:18]5[C:19](=[O:28])[C:20]6[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=6)[C:26]5=[O:27])=[CH:16][C:11]=4[N:10]=[CH:9]3)[CH:5]=[CH:6][CH:7]=2)[CH:30]=1

Participants

8

Reactant 4

HCID 104421,3-PropanediolHCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 67484159HCID 67484159, compound

Product 1

HCID 67484042HCID 67484042, compound

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 2-[1-(3-bromophenyl)-1H-benzimidazol-5-ylmethyl]-isoindole-1,3-dione (1.10 g, 2.54 mmol), 3-pyridineboronic acid (0.47 g, 3.82 mmol), potassium carbonate (1.06 g, 7.63 mmol), 1,3-propanediol (0.92 ml, 12.72 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.1 g) in a mixture of dimethoxyethane (20 ml) and water (10 ml) was stirred at reflux in a nitrogen atmosphere for 20 min. The resultant mixture was cooled and volatile material was removed in vacuo. The product precipitated from the residual solvent and was filtered off, washed with water and dried in the air to afford 0.56 g.

Workup

  1. temperatureat reflux in a nitrogen atmosphere for 20 min
  2. customvolatile material was removed in vacuo
  3. customThe product precipitated from the residual solvent
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried in the air
  7. customto afford 0.56 g

Sources & evidence

ORD record
ord-6381813be2f54adbb041045f7d3afc19
Source dataset
uspto-grants-2010_12
Patent number
US07851490B2

Reaction notes

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