Cesium carbonate → HCID 57562451, compound

HRID 1726097Notes

Reaction equation

HRID 1726097 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][CH:49](Br)[CH3:50]>>[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 10796Cesium carbonateHCID 112011,1-DibromoethaneHCID 57562414HCID 57562414, compound

Product 1

HCID 57562451HCID 57562451, compound

Procedure

2.22 g of 5-benzyloxy-3-(1-tert-butoxycarbonyl-5-hydroxy-1H-indol-2-yl)-indazole-1-carboxylic acid tert-butyl ester and 7.8 g of cesium carbonate, in 22 ml of dibromoethane, are stirred at 80° C. (temperature of the oil bath) for 48 hours. The reaction mixture is filtered through sintered glass and the solid is rinsed with 20 ml of dichloromethane. The filtrate is concentrated under vacuum. The reaction crude is purified by flash chromatography on 160 g of silica. The eluent is 100% dichloromethane. 2 g of 5-benzyloxy-3-[5-(2-bromo-ethoxy)-1-tert-butoxycarbonyl-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester are isolated.

Workup

  1. filtrationThe reaction mixture is filtered through sintered glass
  2. washthe solid is rinsed with 20 ml of dichloromethane
  3. concentrationThe filtrate is concentrated under vacuum
  4. customThe reaction crude
  5. customis purified by flash chromatography on 160 g of silica

Sources & evidence

ORD record
ord-c28b03764a0f43ec8c9e93ce12ce2dae
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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