1,3-Propanediol → HCID 131726459, compound

HRID 1354034Notes

Reaction equation

HRID 1354034 reaction equation
Br[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(B(CC)[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)C.[C:28](=[O:31])([O-:30])[O-].[K+].[K+].[CH2:34](O)[CH2:35][CH2:36][OH:37].[O:39]1CCOCC1>>[C:36]([OH:37])(=[O:39])/[CH:35]=[CH:34]/[C:28]([OH:30])=[O:31].[N:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:2]2[N:7]=[N:6][C:5]([N:8]3[CH:14]4[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]4)[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[CH:21]=1

Participants

6

Reactant 5

HCID 104421,3-PropanediolHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 6428513-(Diethylboryl)pyridineHCID 179847604-(6-Bromopyridazin-3-yl)-1,4-diazabicyclo[3.2.2]nonane

Product 1

HCID 131726459HCID 131726459, compound

Procedure

A mixture of 4-(6-bromo-pyridazin-3-yl)-1,4-diazabicyclo[3.2.2]nonane (0.49 g, 1.7 mmol), diethyl-3-pyridylborane (0.38 g, 2.6 mmol), aqueous potassium carbonate (2.6 ml, 2M), palladium(0)tetrakistriphenylphosphine (59 mg, 0.051 mmol), 1,3-propandiol (0.37 ml, 5.1 mmol) and dioxane (5 ml) was stirred at reflux for 15 hours. The mixture was evaporated. Aqueous sodium hydroxide (10 ml, 4M) was added. The mixture was extracted with dichloromethane (3×20 ml). Chromatography on silica gel with dichloromethane, 10% methanol and 1% aqueous ammonia as solvent gave the title compound as an oil. Yield 0.10 g, 21%.

Workup

  1. temperatureat reflux for 15 hours
  2. customThe mixture was evaporated
  3. additionAqueous sodium hydroxide (10 ml, 4M) was added
  4. extractionThe mixture was extracted with dichloromethane (3×20 ml)

Sources & evidence

ORD record
ord-3bd49ec799fb4f47a2141b83a4087a24
Source dataset
uspto-grants-2007_05
Patent number
US07223753B2

Reaction notes

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