1-Acetoxy-2-bromoethane → HCID 67147540, compound

HRID 490489Notes

Reaction equation

HRID 490489 reaction equation
[C:1]([O:4][CH2:5][CH2:6]Br)(=[O:3])[CH3:2].[CH3:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([O:19][CH3:20])=[C:15]([OH:18])[CH:16]=2)[C:11]([C:21]2[N:29]([S:30]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[C:24]3=[N:25][CH:26]=[CH:27][CH:28]=[C:23]3[CH:22]=2)=[CH:10]1>>[CH3:20][O:19][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][C:15]=1[O:18][CH2:6][CH2:5][O:4][C:1](=[O:3])[CH3:2])[N:9]([CH3:8])[CH:10]=[C:11]2[C:21]1[N:29]([S:30]([C:33]2[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][CH:38]=2)(=[O:32])=[O:31])[C:24]2=[N:25][CH:26]=[CH:27][CH:28]=[C:23]2[CH:22]=1

Participants

3

Reactant 2

HCID 135641-Acetoxy-2-bromoethaneHCID 22477326HCID 22477326, compound

Product 1

HCID 67147540HCID 67147540, compound

Procedure

2-[5-Methoxy-6-(2-acetyloxyethoxy)-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 0.246 ml of 2-bromoethyl acetate and 0.5 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, 40/60 by volume ethyl acetate/cyclohexane as eluents), 0.506 g of 2-[5-methoxy-6-(2-acetyloxyethoxy)-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine is obtained, the characteristics of which are as follows:

Workup

  1. custom2-[5-Methoxy-6-(2-acetyloxyethoxy)-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine is prepared
  2. customAfter purification by flash-pack chromatography (silica, 40/60 by volume ethyl acetate/cyclohexane as eluents)

Sources & evidence

ORD record
ord-64c6c304704a4884940b4565904b91ef
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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