Methanol → HCID 178471968, compound

HRID 240312

Reaction equation

HRID 240312 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].[H-].[Na+].[O:11]=[C:12]1[C:24]2[C:19](=[N:20][C:21](C#N)=[C:22]([C:25]#[N:26])[N:23]=2)[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]1=2.CO>CN(C=O)C>[C:6]([C:5]([C:21]1[N:20]=[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:12](=[O:11])[C:24]2=[N:23][C:22]=1[C:25]#[N:26])=[C:4]([O:3][CH2:1][CH3:2])[OH:8])#[N:7]

Participants

6

Reactant 4

HCID 887MethanolHCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 2929299-oxo-9H-indeno(1,2-b)pyrazine-2,3-dicarbonitrile

Product 1

HCID 178471968HCID 178471968, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Ethylcyanoacetate (110 mg, 0.970 mmol) was dissolved, under inert atmosphere, in dry DMF (1 ml) and NaH (39 mg, 0.970 mmol) was added in one portion. After 30 min, a solution of 1 (150 mg, 0.646 mmol) in dry DMF (2 ml) was added dropwise. After 15 min MeOH was added and the solution stirred for 10 min. The solvents were evaporated and the crude purified by flash chromatography (EtOAc:MeOH 9:1) affording 22 as a dark red solid (200 mg, 97%).

Workup

  1. customThe solvents were evaporated
  2. customthe crude purified by flash chromatography (EtOAc:MeOH 9:1)

Sources & evidence

ORD record
ord-acdda630ff26422c8d67586bdcbc4117
Source dataset
uspto-grants-2014_02
Patent number
US08648076B2

Linked notes

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