1,3-Propanediol → HCID 131726459、化合物

反応式

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

参加物

反応物 5

HCID 104421,3-Propanediol

HCID 11430Potassium Carbonate

HCID 312751,4-Dioxane

HCID 6428513-(Diethylboryl)pyridine

HCID 179847604-(6-Bromopyridazin-3-yl)-1,4-diazabicyclo[3.2.2]nonane

生成物 1

HCID 131726459HCID 131726459、化合物

実験手順

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%.