Cesium carbonate → [1-Isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-6-methyl-1H-indol-2-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanone

HRID 1786471Notes

Reaction equation

[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][C:19]=2[CH3:20])[NH:16][C:15]([C:21]([N:23]2[CH2:28][CH2:27][N:26]([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:25][CH2:24]2)=[O:22])=[CH:14]3)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[CH:44]([CH3:46])[CH3:45])(=O)=O>>[CH:44]([N:16]1[C:17]2[C:13](=[CH:12][C:11]([O:10][CH:7]3[CH2:8][CH2:9][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:5][CH2:6]3)=[C:19]([CH3:20])[CH:18]=2)[CH:14]=[C:15]1[C:21]([N:23]1[CH2:24][CH2:25][N:26]([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:27][CH2:28]1)=[O:22])([CH3:46])[CH3:45]

Participants

Reactant 3

HCID 10796Cesium carbonate

HCID 13551Isopropyl methanesulfonate

HCID 68563679[5-(1-Isopropyl-piperidin-4-yloxy)-6-methyl-1H-indol-2-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanone

Product 1

HCID 68565510[1-Isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-6-methyl-1H-indol-2-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanoneYield 9%

Procedure

The title compound was synthesized in analogy to example 4, from [5-(1-isopropyl-piperidin-4-yloxy)-6-methyl-1H-indol-2-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanone (example 29), cesium carbonate and isopropyl methanesulfonate, to afford the title compound as a light-yellow oil (9%).

Sources & evidence

ORD record: ord-181aad76998c4b76a9cc21cbd335fd4f
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507736B2

Reaction notes

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