Cesium carbonate → 2-Chloro-6-fluoro-3-methylimidazo[1,2-A]pyridine

HRID 705073Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][N:5]2[C:11]=1I.[CH3:13]B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][N:5]2[C:11]=1[CH3:13]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of the title compound from Example 3 Step A (0.500 g, 1.69 mmol), palladium acetate (0.038 g, 0.169 mmol), methyl boronic acid (0.202 g, 3.37 mmol), cesium carbonate (1.65 g, 5.06 mmol) and triphenyl phosphine (0.088 g, 0.337 mmol) in tetrahydrofuran (8.43 mL) was heated in a sealed tube at 100° C. for 18 hours. The mixture was then cooled to room temperature, filtered, and concentrated under reduced pressure. Purification by flash chromatography on silica gel (0-20% ethyl acetate in hexanes) provided the title compound: LCMS m/z 184.9 [M+H]+ 186.86 [M+2+H]+; 1H NMR (500 MHz, CDCl3) δ 7.75 (d, J=2.4 Hz, 1H), 7.51 (dd, J=9.7, 4.9 Hz, 1H), 7.14-7.102 (m, 1H), 2.44 (s, 3H).

Workup

temperatureThe mixture was then cooled to room temperature
filtrationfiltered
concentrationconcentrated under reduced pressure
customPurification by flash chromatography on silica gel (0-20% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-bc47f146f1a4447899c5ab126c127a0a
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09173873B2

Reaction notes

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