Sodium ethoxide → 2-Ethoxy-6-iodo-3-methoxypyridine

HRID 1675968Notes

Reaction equation

Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([I:10])[N:3]=1.[O-:11][CH2:12][CH3:13].[Na+]>CN(C=O)C>[CH2:12]([O:11][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([I:10])[N:3]=1)[CH3:13]

Participants

Conditions

Temperature: 100 °C

Procedure

In a microwave vial, 2-bromo-6-iodo-3-methoxypyridine (16-1 or 131-3, 150 mg, 0.48 mmol, 1 equiv) was dissolved in DMF (300 uL). Sodium ethoxide (268 uL, 21 wt % in EtOH, 0.72 mmol, 1.5 equiv) was added to the solution, and the reaction was heated in the microwave for 5 minutes at 100° C. The reaction mixture was partitioned between saturated NaHCO3 and DCM. The organic phase was washed once with brine, dried over Mg2SO4 and concentrated. The residue was purified by normal phase column chromatography (0-20% EtOAc in hexanes) to give the title compound (16-2). ESI+MS [M+H]+ C8H11INO2: 280.0 found, 280.1 required.

Workup

customThe reaction mixture was partitioned between saturated NaHCO3 and DCM
washThe organic phase was washed once with brine
dry with materialdried over Mg2SO4
concentrationconcentrated
customThe residue was purified by normal phase column chromatography (0-20% EtOAc in hexanes)

Sources & evidence

ORD record: ord-a3ba955cd1884ce4b1962aca29862f3e
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003797B2

Reaction notes

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