Imidazole → 3-[1-tert-butoxycarbonyl-5-(2-morpholin-4-ylethoxy)-1H-indol-2-yl]-5-(methylphenylphosphinoyloxy)indazole-1-carboxylic acid tert-butyl ester

HRID 1726063Notes

Reaction equation

HRID 1726063 reaction equation
N1C=CN=C1.[CH3:6][P:7](Cl)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].[C:16]([O:20][C:21]([N:23]1[C:31]2[C:26](=[CH:27][C:28]([OH:32])=[CH:29][CH:30]=2)[C:25]([C:33]2[N:34]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[C:35]3[C:40]([CH:41]=2)=[CH:39][C:38]([O:42][CH2:43][CH2:44][N:45]2[CH2:50][CH2:49][O:48][CH2:47][CH2:46]2)=[CH:37][CH:36]=3)=[N:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>ClCCl>[C:16]([O:20][C:21]([N:23]1[C:31]2[C:26](=[CH:27][C:28]([O:32][P:7]([CH3:6])([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:8])=[CH:29][CH:30]=2)[C:25]([C:33]2[N:34]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[C:35]3[C:40]([CH:41]=2)=[CH:39][C:38]([O:42][CH2:43][CH2:44][N:45]2[CH2:50][CH2:49][O:48][CH2:47][CH2:46]2)=[CH:37][CH:36]=3)=[N:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 795Imidazole2×HCID 21983Methyl(phenyl)phosphinoyl chloride2×HCID 57562455HCID 57562455, compound

Product 1

HCID 688433583-[1-tert-butoxycarbonyl-5-(2-morpholin-4-ylethoxy)-1H-indol-2-yl]-5-(methylphenylphosphinoyloxy)indazole-1-carboxylic acid tert-butyl esterYield 31.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

16 mg of imidazole and 40.5 mg of methylphenylphosphinic chloride are added to a solution of 27 mg of 3-[1-tert-butoxycarbonyl-5-(2-morpholin-4-yl-ethoxy)-1H-indol-2-yl]-5-hydroxyindazole-1-carboxylic acid tert-butyl ester in 2 ml of dichloromethane. The solution obtained is stirred at ambient temperature. After stirring for 15 hours, a further 16 mg of imidazole and 40.5 mg of methylphenylphosphinic chloride are added and the mixture is stirred at ambient temperature for another 3½ hours in order for the reaction to be complete. The reaction mixture is then filtered and evaporated under reduced pressure in a rotary evaporator. The residue obtained is purified by LC/MS to obtain 10.5 mg of 3-[1-tert-butoxycarbonyl-5-(2-morpholin-4-ylethoxy)-1H-indol-2-yl]-5-(methylphenylphosphinoyloxy)indazole-1-carboxylic acid tert-butyl ester.

Workup

  1. customThe solution obtained
  2. stirringAfter stirring for 15 hours
  3. stirringthe mixture is stirred at ambient temperature for another 3½ hours in order for the reaction
  4. filtrationThe reaction mixture is then filtered
  5. customevaporated under reduced pressure in a rotary evaporator
  6. customThe residue obtained
  7. customis purified by LC/MS

Sources & evidence

ORD record
ord-2f50332a2c0241108501eb05407d4964
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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