Hydrochloric Acid → HCID 178527072, compound

HRID 1726057Notes

Reaction equation

HRID 1726057 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][P:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:19])=[CH:14][CH:15]=2)[C:10]([CH:32]2[CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]2C(OC(C)(C)C)=O)=[N:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[NH:33]1[C:34]2[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:40][CH:32]1[C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([O:17][P:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:19])[CH:12]=2)[NH:8][N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 68841301HCID 68841301, compound

Product 1

HCID 178527072HCID 178527072, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

A solution of 200 mg of 3-(1-tert-butoxycarbonyl-2,3-dihydro-1H-indol-2-yl)-5-(diphenylphosphinoyloxy)indazole-1-carboxylic acid tert-butyl ester in 4 ml of dioxane and 1 ml of a 4M hydrochloric acid solution in dioxane is stirred at ambient temperature. After 1 hour, 1 ml of a 4M hydrochloric acid solution in dioxane is added. The reaction medium is stirred overnight at ambient temperature. The suspension is filtered through sintered glass. The solid is rinsed with ethyl ether. The solid is taken up in 200 ml of dichloromethane and 8 ml of a 2N aqueous sodium hydroxide solution. The solution is stirred for a few minutes and is then separated by settling out. The organic phase is dried over magnesium sulfate, filtered, and concentrated under reduced pressure to obtain 114 mg of diphenylphosphinic acid 3-(2,3-dihydro-1H-indol-2-yl)-1H-indazol-5-yl ester.

Workup

  1. filtrationThe suspension is filtered through sintered glass
  2. washThe solid is rinsed with ethyl ether
  3. stirringThe solution is stirred for a few minutes
  4. customis then separated
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e0fb9286d94a4d37bbcc673aa7df27f0
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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