1,2-Dibromoethane → HCID 57562451, compound

HRID 1726060Notes

Reaction equation

HRID 1726060 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:15]=2)[C:10]([C:25]2[N:26]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:27]3[C:32]([CH:33]=2)=[CH:31][C:30]([OH:34])=[CH:29][CH:28]=3)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[Br:48][CH2:49][CH2:50]Br>>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:14][CH:15]=2)[C:10]([C:25]2[N:26]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:27]3[C:32]([CH:33]=2)=[CH:31][C:30]([O:34][CH2:50][CH2:49][Br:48])=[CH:29][CH:28]=3)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 57562414HCID 57562414, compound

Product 1

HCID 57562451HCID 57562451, compound

Procedure

A suspension of 2.22 g of 5-benzyloxy-3-(1-tert-butoxycarbonyl-5-hydroxy-1H-indol-2-yl)indazole-1-carboxylic acid tert-butyl ester and of 3.90 g of cesium carbonate in 22 ml of 1,2-dibromoethane is heated at 80° C. for 40 hours and then cooled to ambient temperature and evaporated under reduced pressure in a rotary evaporator. The reaction crude is purified by flash chromatography (silica 40-63 μm), eluent: dichloromethane; 2 g of 5-benzyloxy-3-[5-(2-bromoethoxy)-1-tert-butoxycarbonyl-1H-indol-2-yl]-indazole-1-carboxylic acid tert-butyl ester are isolated.

Workup

  1. customevaporated under reduced pressure in a rotary evaporator
  2. customThe reaction crude
  3. customis purified by flash chromatography (silica 40-63 μm), eluent

Sources & evidence

ORD record
ord-9e9fa69682044c59978a321ec4ef9bde
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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