N-Iodosuccinimide → HCID 178467033, compound

HRID 1050134Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([OH:10])[CH:5]=1)[CH3:2].C1C(=O)N([I:18])C(=O)C1>CN(C=O)C>[CH2:1]([O:3][C:4]1[C:9]([I:18])=[CH:8][N:7]=[C:6]([OH:10])[CH:5]=1)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 4-ethoxypyridin-2-ol (17 g, 122 mmol) in DMF (125 mL) was added NIS (27.5 g, 122 mmol). The mixture was stirred at 80° C. for 16 h. The mixture was concentrated and purified by preparative HPLC (MeCN/H2O as eluants, acidic condition) to yield a yellow solid of 4-ethoxy-5-iodopyridin-2-ol (4.2 g, 13.47 mmol, 11% yield). TLC (DCM/MeOH=10:1, Rf=0.6): 1H NMR (400 MHz, MeOH-d4) δ 7.70 (s, 1H), 5.91 (s, 1H), 4.10 (q, J=7.2 Hz, 2H), 1.44 (t, J=6.8 Hz, 3H); ES-LCMS m/z: 265.9 (M+H).

Workup

concentrationThe mixture was concentrated
custompurified by preparative HPLC (MeCN/H2O as eluants, acidic condition)

Sources & evidence

ORD record: ord-6a36442c5f08496db7ea3ca35633190c
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382238B2

Reaction notes

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