Cesium carbonate → HCID 66781535, compound

HRID 1095746Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][N:10]3[C:13]([C:16]4[CH:25]=[CH:24][C:23]5[C:18](=[C:19]([OH:26])[CH:20]=[CH:21][CH:22]=5)[N:17]=4)=[CH:14][N:15]=[C:9]3[CH:8]=2)[CH:2]=1.[F:27][C@H:28]1[C@@H:33](OS(C)(=O)=O)[CH2:32][CH2:31][N:30]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:29]1.C([O-])([O-])=O.[Cs+].[Cs+].CC(N(C)C)=O>O.CCOC(C)=O>[F:27][C@H:28]1[C@H:33]([O:26][C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:18]=2[N:17]=[C:16]([C:13]2[N:10]4[CH:11]=[CH:12][C:7]([C:3]5[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=5)=[CH:8][C:9]4=[N:15][CH:14]=2)[CH:25]=[CH:24]3)[CH2:32][CH2:31][N:30]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:29]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-(7-(pyridin-3-yl)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ol (30.2 mg, 0.089 mmol), tert-butyl cis-3-fluoro-4-(methylsulfonyloxy)piperidine-1-carboxylate (39.8 mg, 0.134 mmol) and Cs2CO3 (43.6 mg, 0.134 mmol) in DMA (7.78 mg, 0.089 mmol) was heated to 100° C. for 1 hour. The reaction mixture was cooled to ambient temperature and diluted with water and EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by preparative TLC, eluting with 10% MeOH 0.5% NH4OH in DCM to provide the desired product (22 mg, 46% yield).

Workup

temperatureThe reaction mixture was cooled to ambient temperature
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by preparative TLC
washeluting with 10% MeOH 0.5% NH4OH in DCM

Sources & evidence

ORD record: ord-2625319addc44996880546f069b665da
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138181B2

Reaction notes

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