Potassium Hydroxide → 4-chloro-2-[5,6-dimethoxy-1-(2-morpholin-4-ylethyl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine

HRID 490439Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:9]([C:11]3[C:19]4[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=4)[N:13]([CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[CH:12]=3)=[CH:10][C:3]=12.[OH-].[K+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([C:11]3[C:19]4[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=4)[N:13]([CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[CH:12]=3)=[CH:10][C:3]=12

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 0.54 g of 4-chloro-2-[5,6-dimethoxy-1-(2-morpholin-4-ylethyl)-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine and 1.8 g of potassium hydroxide in 18 ml of methanol is brought to around 60° C. for approximately 2 hours. After cooling to approximately 20° C., the precipitate is filter-dried, washed with two times 3 ml of methanol and three times 5 ml of water, and then dried in an oven under reduced pressure (13 kPa) at a temperature in the region of 40° C. for approximately 8 hours. 0.241 g of 4-chloro-2-[5,6-dimethoxy-1-(2-morpholin-4-ylethyl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine is obtained in the form of a solid, the characteristics of which are as follows:

Workup

customthe precipitate is filter-dried
washwashed with two times 3 ml of methanol and three times 5 ml of water
customdried in an oven under reduced pressure (13 kPa) at a temperature in the region of 40° C. for approximately 8 hours

Sources & evidence

ORD record: ord-e18367be7278462599d00f0d87e6eb34
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528147B2

Reaction notes

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