1,3-Propanediol → HCID 17984761, compound

HRID 1354032Notes

Reaction equation

HRID 1354032 reaction equation
[Br:1][C:2]1[N:3]=[N:4][C:5](Br)=[CH:6][CH:7]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].C(O)CCO.[S:33]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34]1.[OH-].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[Br:1][C:2]1[N:3]=[N:4][C:5]([C:35]2[CH:36]=[CH:37][S:33][CH:34]=2)=[CH:6][CH:7]=1

Participants

9

Reactant 6

HCID 104421,3-PropanediolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2488523,6-DibromopyridazineHCID 581760Thiophene-3-boronic acid

Product 1

HCID 17984761HCID 17984761, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3,6-dibromo-pyridazine (8.45 g, 35.5 mmol), palladacycle (0.66 g, 0.71 mmol), palladium acetate (0.16 g, 0.71 mmol), tri-tert-butylphosphine (0.35 ml, 1.42 mmol), aqueous potassium carbonate (2 M, 107 mmol), 1,3-propanediol (7.7 ml, 107 mmol) and 1,4-dioxane (100 ml) was stirred at reflux for 1 hour. 3-Thienyl boronic acid (5.0 g, 39.0 mmol) was added and the mixture was stirred at reflux for 7 days. Aqueous sodium hydroxide (50 ml, 1M) was added and the mixture was extracted with ethyl acetate (2×100 ml). Chromatography on silica gel with ethyl acetate:petroleum (1:3) as solvent gave the title compound. Yield 1.5 g (18%).

Workup

  1. temperatureat reflux for 1 hour
  2. stirringthe mixture was stirred
  3. temperatureat reflux for 7 days
  4. extractionthe mixture was extracted with ethyl acetate (2×100 ml)

Sources & evidence

ORD record
ord-55f1a3f289984f0bbcf960bbf373d546
Source dataset
uspto-grants-2007_05
Patent number
US07223753B2

Reaction notes

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