Potassium Hydroxide → HCID 67148071, compound

HRID 2426911Notes

Reaction equation

FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]([CH3:21])[CH:14]=[C:13]2[C:22]1[N:38](S(C2C=CC(C)=CC=2)(=O)=O)[C:25]2=[N:26][CH:27]=[CH:28][C:29]([CH2:30][NH:31][C:32]3[N:33]([CH3:37])[N:34]=[CH:35][CH:36]=3)=[C:24]2[CH:23]=1.[OH-].[K+]>>[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]([CH3:21])[CH:14]=[C:13]2[C:22]1[NH:38][C:25]2=[N:26][CH:27]=[CH:28][C:29]([CH2:30][NH:31][C:32]3[N:33]([CH3:37])[N:34]=[CH:35][CH:36]=3)=[C:24]2[CH:23]=1

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 67147526HCID 67147526, compound

Product 1

HCID 67148071HCID 67148071, compoundYield 49.3%

Procedure

[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl](2-methyl-2H-pyrazol-3-yl)amine is prepared as described in Example 179a starting with 0.08 g of [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl](2-methyl-2H-pyrazol-3-yl)amine trifluoroacetate instead of the [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl](4-trifluoromethylsulfanylbenzyl)amine used in Example 179a and 0.62 cm3 of 5N potassium hydroxide. After purification by flash-pack chromatography (SiO2, dichloromethane/methanol 98/02 by volume as eluent), 0.024 g of [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl](2-methyl-2H-pyrazol-3-yl)amine is obtained, the characteristics of which are as follows:

Workup

custom[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl](2-methyl-2H-pyrazol-3-yl)amine is prepared
customAfter purification by flash-pack chromatography (SiO2, dichloromethane/methanol 98/02 by volume as eluent)

Sources & evidence

ORD record: ord-868da90136a544cb98b807cc5a26ed0a
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968566B2

Reaction notes

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