2-Bromoethyl methyl ether → 2-[5-methoxy-6-(2-methoxyethoxy)-1-methyl-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine

HRID 490487Notes

Reaction equation

HRID 490487 reaction equation
Br[CH2:2][CH2:3][O:4][CH3:5].[CH3:6][N:7]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([OH:16])[CH:14]=2)[C:9]([C:19]2[N:27]([S:28]([C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=3)(=[O:30])=[O:29])[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=2)=[CH:8]1>>[CH3:18][O:17][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][C:13]=1[O:16][CH2:2][CH2:3][O:4][CH3:5])[N:7]([CH3:6])[CH:8]=[C:9]2[C:19]1[N:27]([S:28]([C:31]2[CH:32]=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=2)(=[O:30])=[O:29])[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[CH:20]=1.[CH3:18][O:17][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][C:13]=1[O:16][CH2:2][CH2:3][O:4][CH3:5])[N:7]([CH3:6])[CH:8]=[C:9]2[C:19]1[NH:27][C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[CH:20]=1

Participants

4

Reactant 2

HCID 809722-Bromoethyl methyl etherHCID 22477326HCID 22477326, compound

Product 2

HCID 67147655HCID 67147655, compoundHCID 671476952-[5-methoxy-6-(2-methoxyethoxy)-1-methyl-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridineYield 137.6%

Procedure

2-[5-Methoxy-6-(2-methoxyethoxy)-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine is prepared by following the procedure described in example 147d, but using 0.195 g of 1-bromo-2-methoxyethane instead of 1-chloro-2-bromoethane used in example 147d, and 0.224 g of 2-[1-methyl-5-methoxy-6-hydroxyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine. After purification by flash-pack chromatography (silica, 80/20 by volume ethyl acetate/cyclohexane as eluents, argon), 0.121 g of 2-[5-methoxy-6-(2-methoxyethoxy)-1-methyl-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine is obtained, the characteristics of which are as follows:

Workup

  1. customAfter purification by flash-pack chromatography (silica, 80/20 by volume ethyl acetate/cyclohexane as eluents, argon)

Sources & evidence

ORD record
ord-80272c72b25f4ec393ce29bb3f531f41
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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