1-Bromo-2-Chloroethane → 5-benzyloxy-3-[1-tert-butoxycarbonyl-5-(2-chloro-ethoxy)-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester

HRID 1726086Notes

Reaction equation

HRID 1726086 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].Br[CH2:43][CH2:44][Cl:45].[OH-].[Na+]>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[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][CH2:43][CH2:44][Cl:45])=[CH:29][CH:28]=3)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 57562414HCID 57562414, compound

Product 1

HCID 575624225-benzyloxy-3-[1-tert-butoxycarbonyl-5-(2-chloro-ethoxy)-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 100 mg of 5-benzyloxy-3-(1-tert-butoxycarbonyl-5-hydroxy-1H-indol-2-yl)indazole-1-carboxylic acid tert-butyl ester and 132 μl of 1-bromo-2-chloroethane in 5 ml of dichloromethane is mixed with an aqueous solution of 72 mg of tetrabutylammonium bromide and of 270 μl of 2N sodium hydroxide in 5 ml of distilled water. The reaction mixture is stirred vigorously at 20° C. for 6 hours. After separation by settling out and washing with water (4×5 ml), the organic extracts are combined, dried over magnesium sulfate and then evaporated under reduced pressure. The crude compound obtained is purified by preparative LC/MS. The fractions containing the expected compound are combined and evaporated under reduced pressure to obtain 18.1 mg of 5-benzyloxy-3-[1-tert-butoxycarbonyl-5-(2-chloroethoxy)-1H-indol-2-yl]-indazole-1-carboxylic acid tert-butyl ester, which is characterized as follows:

Workup

  1. customAfter separation
  2. washwashing with water (4×5 ml)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe crude compound obtained
  6. customis purified by preparative LC/MS
  7. additionThe fractions containing the expected compound
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6d393803291a472395ac13d94b518bc9
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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