6-Chloro-2-iodothieno[2,3-b]pyridine → 6-Chlorothieno[2,3-b]pyridine-2-carbonitrile

HRID 1465754Notes

Reaction equation

HRID 1465754 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[S:8][C:9](I)=[CH:10][C:5]2=[CH:4][CH:3]=1.[Cu][C:13]#[N:14]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]2[S:8][C:9]([C:13]#[N:14])=[CH:10][C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 895251046-Chloro-2-iodothieno[2,3-b]pyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 895263326-Chlorothieno[2,3-b]pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 6-Chloro-2-iodothieno[2,3-b]pyridine (80 mg, 0.27 mmol) and Copper (I) Cyanide (36 mg, 0.41 mmol) in DMF (3 mL) was heated to 130° C. for 16 hrs. LC showed formation of the title product. The crude reaction was adsorbed onto silica gel, and purified by flash chromatography to obtain the title product. LC-MS (IE, m/z): 195 [M+1]+.

Sources & evidence

ORD record
ord-e01035dc66a94ca280f2082a95818aac
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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