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

HRID 383312Notes

Reaction equation

Br[C:2]1[N:6]2[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[Cl:12][C:13]1[CH:18]=[C:17](B(O)O)[CH:16]=[CH:15][N:14]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:17]3[CH:16]=[CH:15][N:14]=[C:13]([Cl:12])[CH:18]=3)=[CH:3][N:4]=2)[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-bromo-6-chloro-imidazo[1,2-a]pyridine (1 eq, 18.1 mmol, 4.2 g), 2-chloropyridin-4-yl boronic acid (1.05 eq, 19 mmol, 3 g), Na2CO3 (2 eq, 36.2 mmol, 3.84 g) in dioxane (30 ml) and water (10 ml), under an inert atmosphere of argon is added bis(triphenylphosphine)palladium II chloride (1.23 g). The reaction mixture is heated at 100° C. for 16 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 0-50% EtOAc in iso-hexane to afford the title compound; [M+H]+=264 (266).

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 0-50% EtOAc in iso-hexane

Sources & evidence

ORD record: ord-ca169e7cd1ac457d8b4a67956b0cf0f8
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367662B2

Reaction notes

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