N-Iodosuccinimide → 3-(3-Iodo-imidazo[1,2-a]pyridin-6-yl)-but-2-enoic acid methyl ester

HRID 1394648Notes

Reaction equation

[I:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11](=[O:24])[CH:12]=[C:13]([C:15]1[CH:16]=[CH:17][C:18]2[N:19]([CH:21]=[CH:22][N:23]=2)[CH:20]=1)[CH3:14]>C(#N)C.C(OCC)(=O)C>[CH3:9][O:10][C:11](=[O:24])[CH:12]=[C:13]([C:15]1[CH:16]=[CH:17][C:18]2[N:19]([C:21]([I:1])=[CH:22][N:23]=2)[CH:20]=1)[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

N-iodosuccinimide (252 mg, 1.12 mmol) was added to a mixture of 3-imidazo[1,2-a]pyridin-6-yl-but-2-enoic acid methyl ester (220 mg, 1.02 mmol) in acetonitrile (10 mL) which had been cooled to 0° C. under nitrogen atmosphere. The mixture was stirred for 1 h, then diluted with ethyl acetate (30 mL) and washed with saturated sodium bicarbonate solution (2×10 mL), and brine (1×15 mL). The organic layers were combined, dried over MgSO4 and concentrated in vacuo. The residue was purified by chromatography (chromatotron, 4μ plate, 50% ethyl acetate in hexanes) to yield 3-(3-iodo-imidazo[1,2-a]pyridin-6-yl)-but-2-enoic acid methyl ester as a pale yellow solid (168.1 mg, 48%). 1H NMR (250 MHz, CDCl3): δ 8.27 (bs, 1H), 7.77 (s, 1H), 7.64 (d, 1H, J=9.4), 7.41 (dd, 1H, J=9.4, J=1.6), 6.27 (d, 1H, J=0.62), 3.84 (s, 3H), 2.68 (d, 3H, J=0.62). MS [EI+] 343 (M+H)+.

Workup

washwashed with saturated sodium bicarbonate solution (2×10 mL), and brine (1×15 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by chromatography (chromatotron, 4μ plate, 50% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-4c392342cbf44ba593e1bcccde98c3f7
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348359B2

Reaction notes

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