2-Ethoxy-6-iodo-3-methoxypyridine → HCID 57484717, compound

HRID 1802355Notes

Reaction equation

HRID 1802355 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[C:6](I)[N:5]=1)[CH3:2].[Cu](C#N)[C:14]#[N:15]>CN(C=O)C>[CH2:1]([O:3][C:4]1[N:5]=[C:6]([C:14]#[N:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]

Participants

4

Reactant 2

HCID 574847182-Ethoxy-6-iodo-3-methoxypyridineHCID 178418260HCID 178418260, compound

Product 1

HCID 57484717HCID 57484717, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2-ethoxy-6-iodo-3-methoxypyridine (10-2, 100 mg, 0.36 mmol, 1 equiv) in DMF (675 uL) was added copper cyanide (39 mg, 0.43, mmol, 1.2 equiv). The reaction mixture was heated in a microwave reactor at 150° C. for 20 minutes, and then was partitioned between DCM (50 mL) and water (50 mL). The aqueous layer was extracted with DCM (3×25 mL), and the organic phase was dried over Mg2SO4, concentrated and purified by normal phase column chromatography (20-50% EtOAc in hexanes) to yield the title compound (10-3) as a white solid. ESI+MS [M+H]+ C9H11N2O2: 179.1 found, 179.2 required.

Workup

  1. customwas partitioned between DCM (50 mL) and water (50 mL)
  2. extractionThe aqueous layer was extracted with DCM (3×25 mL)
  3. dry with materialthe organic phase was dried over Mg2SO4
  4. concentrationconcentrated
  5. custompurified by normal phase column chromatography (20-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-905e711e4660466a836f901533c9546f
Source dataset
uspto-grants-2013_01
Patent number
US08349872B2

Reaction notes

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