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

HRID 876785Notes

Reaction equation

HRID 876785 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-82304ddb3b624693aa5847a20849ccdc
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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