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

HRID 1726064Notes

Reaction equation

HRID 1726064 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][P:18]([CH3:26])([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:19])=[CH:14][CH:15]=2)[C:10]([C:27]2[N:28](C(OC(C)(C)C)=O)[C:29]3[C:34]([CH:35]=2)=[CH:33][C:32]([O:36][CH2:37][CH2:38][N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)=[CH:31][CH:30]=3)=[N:9]1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[N:39]1([CH2:38][CH2:37][O:36][C:32]2[CH:33]=[C:34]3[C:29](=[CH:30][CH:31]=2)[NH:28][C:27]([C:10]2[C:11]4[C:16](=[CH:15][CH:14]=[C:13]([O:17][P:18]([CH3:26])([C:20]5[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=5)=[O:19])[CH:12]=4)[NH:8][N:9]=2)=[CH:35]3)[CH2:40][CH2:41][O:42][CH2:43][CH2:44]1

Participants

4

Reactant 1

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

Product 1

HCID 136055981methylphenylphosphinic acid 3-[5-(2-morpholin-4-ylethoxy)-1H-indol-2-yl]-1H-indazol-5-yl esterYield 67.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 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 in a mixture of 500 μl of dichloromethane and 500 μl of trifluoroacetic acid is agitated at ambient temperature for 4 hours. The reaction medium is evaporated under a stream of nitrogen and then redissolved in 1.4 ml of DMSO. The solution obtained is stirred at 60° C. for 3 days and then purified by LC/MS to obtain 5.1 mg of methylphenylphosphinic acid 3-[5-(2-morpholin-4-ylethoxy)-1H-indol-2-yl]-1H-indazol-5-yl ester.

Workup

  1. customThe reaction medium is evaporated under a stream of nitrogen
  2. dissolutionredissolved in 1.4 ml of DMSO
  3. customThe solution obtained
  4. stirringis stirred at 60° C. for 3 days
  5. custompurified by LC/MS

Sources & evidence

ORD record
ord-b8974f823db44c37ab467e332fd24770
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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