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

HRID 1802354Notes

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 (10-1 or 3-3, 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 (10-2). 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-dc8a01f349ae4732abff676850c60097
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349872B2

Reaction notes

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