Cyanoacetamide → (2E)-3-(1-benzyl-2-ethoxy-1H-indol-3-yl)-2-cyanoacrylamide

HRID 1158728Notes

Reaction equation

HRID 1158728 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].C[O-].[Na+].F[B-](F)(F)F.[CH2:15]([N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([CH:31]=[N+](C)C)=[C:23]1[O:35][CH2:36][CH3:37])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO>[CH2:15]([N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24](/[CH:31]=[C:3](\[C:1]#[N:2])/[C:4]([NH2:6])=[O:5])=[C:23]1[O:35][CH2:36][CH3:37])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 10942334Sodium MethoxideHCID 86614832N-[(1-benzyl-2-ethoxy-1H-indol-3-yl)methylene]-N-methylmethanaminium tetrafluoroborate

Product 1

HCID 59513624(2E)-3-(1-benzyl-2-ethoxy-1H-indol-3-yl)-2-cyanoacrylamideYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of cyanoacetamide (4.60 g, 54.7 mmol) and NaOMe (0.5 M solution in MeOH, 80 mL, 4 mmol) was added a solution of (N-[(1-benzyl-2-ethoxy-1H-indol-3-yl)methylene]-N-methylmethanaminium tetrafluoroborate (v-a, 27.6 mmol) in MeOH (120 mL). The reaction was stirred at RT under an atmosphere of Ar. After 15 h, the reaction was cooled to 0° C. and was quenched by the addition of water. The insoluble product was filtered, triturated in MeOH and refiltered to yield a yellow solid (2E)-3-(1-benzyl-2-ethoxy-1H-indol-3-yl)-2-cyanoacrylamide (vi-a, 5.68 g, 60%). NH4OAc QC conditions. DAD Retention Time =1.78 min. M+H=346.

Workup

  1. temperaturethe reaction was cooled to 0° C.
  2. customwas quenched by the addition of water
  3. filtrationThe insoluble product was filtered
  4. customtriturated in MeOH

Sources & evidence

ORD record
ord-3bf814cde8184321a55ddb9634fb6de4
Source dataset
uspto-grants-2010_10
Patent number
US07812018B2

Reaction notes

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