Sodium Iodide → 4-Iodo-8-methoxy-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinoline

HRID 1095696Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[C:10][C:11]([C:13]2[N:17]3[CH:18]=[CH:19][C:20]([O:22][CH2:23][CH2:24][O:25][CH3:26])=[CH:21][C:16]3=[N:15][CH:14]=2)=O)[C:4]=1[NH:27]C(=O)OC(C)(C)C.[I-:35].[Na+]>C(O)(=O)C.C(O)=O>[I:35][C:9]1[C:5]2[C:4](=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][CH:6]=2)[N:27]=[C:11]([C:13]2[N:17]3[CH:18]=[CH:19][C:20]([O:22][CH2:23][CH2:24][O:25][CH3:26])=[CH:21][C:16]3=[N:15][CH:14]=2)[CH:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To tert-butyl 2-methoxy-6-(3-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)-3-oxoprop-1-ynyl)phenylcarbamate (2.51 g, 5.39 mmol) and sodium iodide (16.2 g, 108 mmol) was added acetic acid/formic acid (5 mL/5 mL). The reaction vessel was purged with N2 and heated to 60° C. for 3 hours. The reaction was then cooled to ambient temperature and diluted with H2O/DCM (50 mL/100 mL), followed by extraction with DCM. The combined organics were washed with saturated NaHCO3, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (EtOAc/MeOH 10:1) provided the desired product (92%).

Workup

customThe reaction vessel was purged with N2
temperatureThe reaction was then cooled to ambient temperature
additiondiluted with H2O/DCM (50 mL/100 mL)
extractionfollowed by extraction with DCM
washThe combined organics were washed with saturated NaHCO3
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography (EtOAc/MeOH 10:1)

Sources & evidence

ORD record: ord-73e4a9c2aed1428ea1de1f66e65f3e43
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138181B2

Reaction notes

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