Cesium carbonate → HCID 58547260, compound

HRID 1850342Notes

Reaction equation

Cl.[NH:2]1[CH2:5][CH:4]([C:6]2[C:11]([C:12]3[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=3)=[N:10][CH:9]=[CH:8][N:7]=2)[CH2:3]1.Cl[C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[C:14]1([CH3:18])[CH:15]=[CH:16][CH:17]=[C:12]([C:11]2[C:6]([CH:4]3[CH2:5][N:2]([C:20]4[CH:29]=[CH:28][C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:21]=4)[CH2:3]3)=[N:7][CH:8]=[CH:9][N:10]=2)[CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-azetidin-3-yl-3-m-tolyl-pyrazine hydrochloride (131 mg, 0.05 mmol) and 2-chloro-quinoline (82 mg, 0.05 mmol) in DMF (10 mL) was added Cs2CO3 (325 mg, 1.0 mmol). The reaction mixture was stirred at 100° C. overnight. The reaction mixture was diluted with water, extracted with EtOAc (30 mL×2). The combined organic extracts were washed with water (30 mL) and brine (30 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (20% to 40% EtOAc in petroleum ether) to give 2-[3-(3-m-tolyl-pyrazin-2-yl)-azetidin-1-yl]-quinoline (44 mg, 0.13 mmol, 25%).

Workup

extractionextracted with EtOAc (30 mL×2)
washThe combined organic extracts were washed with water (30 mL) and brine (30 mL)
dry with materialdried over Na2SO4
filtrationfiltered
customThe filtrate was evaporated in vacuo
customthe residue was purified by flash column chromatography on silica gel (20% to 40% EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-ea1f72746f8c44de9695dc39fd95b14b
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957073B2

Reaction notes

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