Dimethylformamide → 2-Iodo-3-(4-methoxy-benzyloxy)-pyridine

HRID 61900

Reaction equation

[I:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C.[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>O>[I:1][C:2]1[C:7]([O:8][CH2:26][C:25]2[CH:28]=[CH:29][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 45 °C

Procedure

2-Iodo-pyridin-3-ol (50 mg, 0.226 mmol), K2CO3 (62 mg, 0.452 mmol) and DMF (2 ml) were added with para-methoxybenzyl chloride (46 μL, 0.339 mmol), and the mixture was stirred overnight at 45° C. The resultant was added with water, and then extracted with ethyl acetate. The organic layer was washed with saturated brine, and the resulting residues obtained after concentration under reduced pressure were purified by silica gel column (ethyl acetate/hexane) to obtain the title compound (21 mg, 27%).

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with saturated brine
customthe resulting residues obtained
concentrationafter concentration under reduced pressure
customwere purified by silica gel column (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-0db4a42840764726a8adfa1e8cbbc81b
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440922B2

Linked notes

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