Dimethylformamide → HCID 67233161, compound

HRID 2368754Notes

Reaction equation

HRID 2368754 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[C:9]([OH:18])=[C:10]2[CH:17]=[CH:16][S:15][C:11]2=[C:12](Br)[N:13]=1)=[O:7])[CH2:2][CH2:3][CH3:4].[C:19]([Cu])#[N:20].CN(C)C=O>O>[CH2:1]([O:5][C:6]([C:8]1[C:9]([OH:18])=[C:10]2[CH:17]=[CH:16][S:15][C:11]2=[C:12]([C:19]#[N:20])[N:13]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 86607517HCID 86607517, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 67233161HCID 67233161, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 7-bromo-4-hydroxy-thieno[2,3-c]pyridine-5-carboxylic acid butyl ester (example 43 a, 165 mg, 0.5 mmol), CuCN (91 mg, 1 mmol), and dimethylformamide (2 ml) was heated in a microwave oven at 160° C. with stirring for 15 min. After cooling to ambient temperature water (20 ml) was added and the mixture was extracted with ethyl acetate (1×60 ml). The resulting mixture was filtered through a pad of celite. The organic phase was washed with water (2×25 ml), dried over MgSO4, and concentrated in vacuo to give the title compound as tan solid (72 mg); MS-(−)-ion: MS-(−)-ion: M−1=275.1.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate (1×60 ml)
  3. filtrationThe resulting mixture was filtered through a pad of celite
  4. washThe organic phase was washed with water (2×25 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4b0c78092bc24a5783867599f9d1c5ea
Source dataset
uspto-grants-2014_04
Patent number
US08703795B2

Reaction notes

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