HCID 67233406, compound → HCID 67234429, compound

HRID 2368730Notes

Reaction equation

HRID 2368730 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[CH:12]=[C:13](Br)[S:14][C:8]=2[C:7]=1[OH:16])=[O:5])[CH3:2].[Cu][C:18]#[N:19]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[CH:12]=[C:13]([C:18]#[N:19])[S:14][C:8]=2[C:7]=1[OH:16])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67233406HCID 67233406, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 67234429HCID 67234429, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-bromo-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid ethyl ester (example 21.d, 150 mg, 0.5 mmol) and copper(I) cyanide (90 mg, 1.0 mmol) suspended in 2 mL DMF was heated at 140° C. for 30 minutes in a CEM microwave reactor. The resultant mixture was partitioned between ethyl acetate and water, and the organic fraction was washed with brine, dried over anhydrous sodium sulfate, and concentrated to a crude residue. The desired product was purified by column chromatography eluting from silica gel with a gradient of 20-70% ethyl acetate in hexanes to give 24 mg of a white solid; MS: (+) m/z 248.9 (M+1)

Workup

  1. customThe resultant mixture was partitioned between ethyl acetate and water
  2. washthe organic fraction was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated to a crude residue
  5. customThe desired product was purified by column chromatography
  6. washeluting from silica gel with a gradient of 20-70% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-1c471e71dbec46e9b63d7c573e026aed
Source dataset
uspto-grants-2014_04
Patent number
US08703795B2

Reaction notes

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