Sodium Carbonate → 3,6-Bis-(2-methoxy-pyridin-4-yl)-imidazo[1,2-a]pyridine

HRID 383287Notes

Reaction equation

Br[C:2]1[N:6]2[CH:7]=[C:8](Br)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.CO[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1B(O)O.[C:23]([O-:26])([O-])=O.[Na+].[Na+].O1[CH2:34][CH2:33][O:32][CH2:31]C1>O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:31][O:32][C:33]1[CH:34]=[C:9]([C:2]2[N:6]3[CH:7]=[C:8]([C:19]4[CH:14]=[CH:15][N:16]=[C:17]([O:26][CH3:23])[CH:18]=4)[CH:9]=[CH:10][C:5]3=[N:4][CH:3]=2)[CH:10]=[CH:5][N:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-bromo-6-bromo-imidazo[1,2-a]pyridine (Intermediate H) (1 eq, 0.72 mmol, 0.2 g), 3-methoxypyrid-4-yl boronic acid (1.0 eq, 0.72 mmol, 0.11 g), Na2CO3 (2 eq, 1.44 mmol, 152 mg) in dioxane (45 ml) and water (13.5 ml) under inert atmosphere of argon is added bis(triphenylphosphine)palladium II chloride (0.1 eq, 0.07 mmol, 50 mg). The reaction mixture is heated at 100° C. for 2 hours. The mixture is diluted with H2O (50 ml) and extracted with EtOAc. The combined organic portions are washed with brine, dried (MgSO4) and concentrated in vacuo. The residue is purified by flash chromatography on silica eluting with 25-75% ethyl acetate in iso-hexane to afford the title compound; [M+H]+=333

Workup

extractionextracted with EtOAc
washThe combined organic portions are washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe residue is purified by flash chromatography on silica eluting with 25-75% ethyl acetate in iso-hexane

Sources & evidence

ORD record: ord-af509ed55152452baa4d792b69e5fe9a
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367662B2

Reaction notes

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