Cesium carbonate → Tert-butyl 4-fluoro-4-((2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)methyl)piperidine-1-carboxylate

HRID 1095718Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[C:18]([OH:25])[CH:19]=[CH:20][CH:21]=4)[N:16]=3)=[CH:13][N:14]=[C:8]2[CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[F:32][C:33]1([CH2:46]OS(C)(=O)=O)[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]1>CC(N(C)C)=O>[F:32][C:33]1([CH2:46][O:25][C:18]2[CH:19]=[CH:20][CH:21]=[C:22]3[C:17]=2[N:16]=[C:15]([C:12]2[N:9]4[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][C:8]4=[N:14][CH:13]=2)[CH:24]=[CH:23]3)[CH2:34][CH2:35][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:37][CH2:38]1

Participants

Conditions

Temperature: 90 °C

Procedure

2-(7-(2-Methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ol (0.050 g, 0.149 mmol) was dissolved in DMA (0.5 mL) and treated with Cs2CO3 (0.097 g, 0.29 mmol). After stirring for several minutes, tert-butyl 4-fluoro-4-((methylsulfonyloxy)methyl)piperidine-1-carboxylate (0.053 g, 0.171 mmol) was added. The mixture was heated to 90° C. for 40 hours. The entire reaction mixture was applied to a SiO2 column and eluted with a gradient from 1-20% (6% NH4OH in MeOH)/ethyl acetate to provide the desired product (11 mg). MS ESI (+) m/z 551.1 (M+1) detected.

Workup

customThe entire reaction mixture
washeluted with a gradient from 1-20% (6% NH4OH in MeOH)/ethyl acetate

Sources & evidence

ORD record: ord-dff27a7891fc496eb809885b724128b8
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138181B2

Reaction notes

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