Water → HCID 58459359, compound

HRID 2036678Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8](I)=[C:9]([C@@H:11]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:12])[N:10]=2)[CH:7]=1.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27](B(O)O)[CH:26]=1.[F-].[Cs+].O>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:27]3[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=3)=[C:9]([C@@H:11]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:12])[N:10]=2)[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (S)-benzyl (1-(6-fluoro-3-iodoimidazo[1,2-a]pyridine-2-yl)ethyl)carbamate (100 mg, 0.22 mmol) and pyridine 3-yl-boronic acid (30.7 mg, 0.25 mmol) in 1,4-dioxane (2 mL) was added cesium fluoride (66.8 mg, 0.440 mmol) at 25° C. The reaction mixture was degassed with nitrogen for 30 min and then tetrakis triphenylphosphine palladium(0) (13 mg, 0.011 mmol) was added at 25° C. The reaction mixture was stirred overnight at 100° C. After completion of the reaction water was added and the mixture extracted with EtOAc. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography using silica gel (100-200 mesh) and 0-4% MeOH in DCM to provide (S)-Benzyl (1-(6-fluoro-3-(pyridine-3-yl)imidazo[1,2-a]pyridine-2-yl)ethyl)carbamate: LC-MS (ESI)] m/z 391.0 [M+H]+.

Workup

customThe reaction mixture was degassed with nitrogen for 30 min
additionwas added
extractionthe mixture extracted with EtOAc
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-320aeab0041343e6bd85d110371cdf89
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575183B2

Reaction notes

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