HCID 59129742, compound → HCID 59129744, compound

HRID 1991459Notes

Reaction equation

HRID 1991459 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:14])=[C:8]([CH2:12][CH3:13])[C:9]=2[CH3:11])[S:4][C:3]=1[C:15]([O:17][CH3:18])=[O:16].[C:19]([Cu])#[N:20]>CN1C(=O)CCC1>[C:19]([C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:14])=[C:8]([CH2:12][CH3:13])[C:9]=2[CH3:11])[S:4][C:3]=1[C:15]([O:17][CH3:18])=[O:16])#[N:20]

Participants

4

Reactant 2

HCID 59129742HCID 59129742, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 59129744HCID 59129744, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To the solution of methyl 3-iodo-5-ethyl-4,6-dimethylthieno[2,3-b]pyridine-2-carboxylate prepared above (5.18 g, 13.8 mmol) in NMP (100 mL), was added CuCN (2.47 g, 27.6 mmol). The mixture was stirred at room temperature overnight. Work-up was conducted as above and the crude product was chromatographed (EtOAc/CH2Cl2, 2.5/97.5) to give pure methyl 3-cyano-5-ethyl-4,6-dimethylthieno[2,3-b]pyridine-2-carboxylate (2.70 g, 71%). MS (ES+) m/z: 275.

Workup

  1. customwas chromatographed (EtOAc/CH2Cl2, 2.5/97.5)

Sources & evidence

ORD record
ord-6e2fca38fb594ae6bdc286bdb645a626
Source dataset
uspto-grants-2010_01
Patent number
US07645881B2

Reaction notes

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