Piperidin-4-ol → HCID 11495762, compound

HRID 490431Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([CH2:14][C:15]([OH:17])=O)[CH:7]=[C:6]2[C:18]1[NH:26][C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]2[CH:19]=1.[OH:27][CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([CH2:14][C:15]([N:31]1[CH2:32][CH2:33][CH:28]([OH:27])[CH2:29][CH2:30]1)=[O:17])[CH:7]=[C:6]2[C:18]1[NH:26][C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]2[CH:19]=1

Participants

Reactant 2

HCID 79341Piperidin-4-ol

HCID 9903065HCID 9903065, compound

Product 1

HCID 11495762HCID 11495762, compoundYield 38.8%

Procedure

2-[5,6-Dimethoxy-3-(1H-pyrrolo[2,3-b]pyridin-2-yl)-indol-1-yl]-1-(4-hydroxypiperidin-1-yl)ethanone is prepared by following the procedure described in example 93, but using 0.2 g of 2-[5,6-dimethoxy-3-(1H-pyrrolo[2,3-b]pyridin-2-yl)indol-1-yl]acetic acid and 0.07 g of 4-hydroxypiperidine. After purification by flash-pack chromatography (silica, 98/02 by volume dichloromethane/methanol as eluents), 0.096 g of 2-[5,6-dimethoxy-3-(1H-pyrrolo[2,3-b]pyridin-2-yl)-indol-1-yl]-1-(4-hydroxypiperidin-1-yl)ethanone is obtained, the characteristics of which are as follows:

Workup

custom2-[5,6-Dimethoxy-3-(1H-pyrrolo[2,3-b]pyridin-2-yl)-indol-1-yl]-1-(4-hydroxypiperidin-1-yl)ethanone is prepared
customAfter purification by flash-pack chromatography (silica, 98/02 by volume dichloromethane/methanol as eluents)

Sources & evidence

ORD record: ord-0ece144255f748b5b0c5895ac340a3ea
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528147B2

Reaction notes

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