3-Bromothieno[2,3-b]pyridine → Thieno[2,3-b]pyridine-3-carbonitrile

HRID 1890539Notes

Reaction equation

HRID 1890539 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[S:4][CH:3]=1.[C:11]([Cu])#[N:12]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:4]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:10]2[C:2]([C:11]#[N:12])=[CH:3]1

Participants

5

Reactant 2

HCID 2899263-Bromothieno[2,3-b]pyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 21828305Thieno[2,3-b]pyridine-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 3-bromothieno[2,3-b]pyridine (J-3) (107 mg, 0.5 mmol) and CuCN (60 mg, 0.67 mmol) in anhydrous DMF (4 mL) was added Pd(PPh3)4 (57 mg, 0.05 mmol). The reaction was degassed with nitrogen and stirred at 120° C. for 5 h. Then the cooled mixture was concentrated and purified by chromatography to afford the title compound. MS (m/z): 161 (M+1)+.

Workup

  1. customThe reaction was degassed with nitrogen
  2. concentrationThen the cooled mixture was concentrated
  3. custompurified by chromatography

Sources & evidence

ORD record
ord-1dd9ac8032c249518067f2ea150d3289
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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