Dimethyl Sulfate → (1H-Pyrrolo[2,3-b]pyridin-3-yl)acetonitrile

反応式

COS(OC)(=O)=O.CN(C)C[N:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[CH:13]=[CH:12]1.[C-]#[N:22].[K+].[CH2:24]1[CH2:28]OCC1>>[NH:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[C:13]([CH2:28][C:24]#[N:22])=[CH:12]1

参加物

反応物 4

HCID 6497Dimethyl Sulfate

HCID 8028Tetrahydrofuran2 回

HCID 9032Potassium Cyanide

HCID 70208500HCID 70208500、化合物

生成物 1

HCID 21911990(1H-Pyrrolo[2,3-b]pyridin-3-yl)acetonitrile収率 56%

反応条件

温度: 80 °C

実験手順

A solution of dimethylsulfate (32.7 g; 0.25 mol) in THF (50 mL) was added dropwise while stirring to the solution of dimethyl-(1H-pyrrolo[2,3-b]-pyridinyl-methyl)-amine (42 g; 0.24 mol) in THF (800 mL). After the addition was complete, the mixture was heated at 80° C. for 10 minutes then cooled to ambient temperature. The solvent was decanted and the residual gum was triturated with acetone/methanol (1:1 mixture) while warming. The solid formed was collected by filtration. The solid was then dissolved in water (500 mL). Potassium cyanide (22 g; 0.32 mol) was added. The mixture was stirred at ambient temperature for 15 minutes, heated to reflux for 30 minutes, then cooled to ambient temperature. After 2 hours, the solid was collected by filtration and washed with water then dried to give 21 g (56% yield) of the title compound as an off-white solid, m.p. 141°-142° C. which was used for the reaction described in step 3.