Piperidin-4-ol → HCID 67147553, compound

HRID 490480Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH3:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([O:22][CH3:23])=[C:15]([O:18][CH2:19][CH2:20]I)[CH:16]=2)[C:11]([C:24]2[N:32]([S:33]([C:36]3[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=3)(=[O:35])=[O:34])[C:27]3=[N:28][CH:29]=[CH:30][CH:31]=[C:26]3[CH:25]=2)=[CH:10]1>>[CH3:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([O:22][CH3:23])=[C:15]([O:18][CH2:19][CH2:20][N:5]3[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]3)[CH:16]=2)[C:11]([C:24]2[N:32]([S:33]([C:36]3[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=3)(=[O:35])=[O:34])[C:27]3=[N:28][CH:29]=[CH:30][CH:31]=[C:26]3[CH:25]=2)=[CH:10]1

Participants

Reactant 2

HCID 79341Piperidin-4-ol

HCID 67147570HCID 67147570, compound

Product 1

HCID 67147553HCID 67147553, compoundYield 92.4%

Procedure

1-{2-[1-methyl-5-methoxy-3-(1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-indol-6-yloxy]ethyl}piperidin-4-ol is prepared by following the procedure described in example 147b, but using 0.089 g of 4-hydroxypiperidine and 0.265 g of 2-[1-methyl-5-methoxy-6-(2-iodoethoxy)-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine. After purification by flash-pack chromatography (silica, 90/10 by volume dichloromethane/methanol as eluents, argon), 0.234 g of 1-{2-[1-methyl-5 methoxy-3-(1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-indol-6-yloxy]ethyl}piperidin-4-ol is obtained, the characteristics of which are as follows:

Workup

custom1-{2-[1-methyl-5-methoxy-3-(1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-indol-6-yloxy]ethyl}piperidin-4-ol is prepared
customAfter purification by flash-pack chromatography (silica, 90/10 by volume dichloromethane/methanol as eluents, argon)

Sources & evidence

ORD record: ord-38f245ea4c0a455cb166194e4a0c6578
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528147B2

Reaction notes

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