Cesium carbonate → 1-ethyl-3-[1-(1,3-thiazol-2-yl)-1H-indol-5-yl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 1044184Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:14]4=[N:15][CH:16]=[CH:17][CH:18]=[C:13]4[N:12]([CH2:19][CH3:20])[C:11]3=[O:21])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl[C:23]1[S:24][CH:25]=[CH:26][N:27]=1.C([O-])([O-])=O.[Cs+].[Cs+].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:19]([N:12]1[C:13]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[N:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[N:1]([C:23]2[S:24][CH:25]=[CH:26][N:27]=2)[CH:2]=[CH:3]3)[C:11]1=[O:21])[CH3:20]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-(2,3-dihydro-1H-indol-5-yl)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (75 mg), 2-chlorothiazole (48.0 mg) and Cs2CO3 (174 mg) in DMF (3 mL) was stirred at 100° C. for 3 days, treated with saturated NaHCO3 solution, and extracted with AcOEt. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. The residue was purified by prep. HPLC and crystallized from AcOEt/Hexane to give the title compound as white crystals (27.0 mg).

Workup

extractionextracted with AcOEt
customThe organic layer was separated
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by prep
customHPLC and crystallized from AcOEt/Hexane

Sources & evidence

ORD record: ord-3686910761e4480ba5172e1a14a34b2c
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563575B2

Reaction notes

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