Cesium carbonate → HCID 88057427, compound

HRID 629865Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:5]2=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:19][C:20]1([F:25])[CH2:22][CH:21]1[CH2:23]I>CN1C(=O)CCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:12])[C:9](=[O:11])[N:10]([CH2:23][CH:21]3[CH2:22][C:20]3([F:25])[F:19])[C:5]2=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

5-Chloro-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1-3, 516 mg, 2.81 mmol) and cesium carbonate (4.97 g, 15.26 mmol) were added to a round bottom flask and suspended in NMP (4.6 mL) under nitrogen. 1,1-Difluoro-2-(iodomethyl)cyclopropane (481 μL, 5.06 mmol) was added to the suspension and then heated to 100° C. in microwave reactor for 10 min. Following this duration, the reaction was cooled to room temperature and suspended in ethyl acetate and sodium bicarbonate. The suspension was washed with sodium bicarbonate, brine(×5), dried over sodium sulfate, filtered, and concentrated. The mixture was purified using reverse-phase chromatography (5-95% 0.1% TFA in H2O:acetonitrile) to give 5-chloro-1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (6-1) as an off-white solid. MS m/z (M+H): calculated=274.0553; observed=274.0551.

Workup

temperaturethe reaction was cooled to room temperature
washThe suspension was washed with sodium bicarbonate, brine(×5)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe mixture was purified

Sources & evidence

ORD record: ord-9943400b9b4f4aaba82048bd45c9c927
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315518B2

Reaction notes

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