Potassium Iodide → 5-benzyloxy-3-[1-tert-butoxycarbonyl-5-(2-diethylaminoethoxy)-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester

HRID 1726089Notes

Reaction equation

HRID 1726089 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:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:27]3[C:32]([CH:33]=2)=[CH:31][C:30]([O:34][CH2:35][CH2:36]Cl)=[CH:29][CH:28]=3)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:53]([NH2:55])[CH3:54].[C:56](#N)[CH3:57]>C(OCC)(=O)C.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:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:15]=2)[C:10]([C:25]2[N:26]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:27]3[C:32]([CH:33]=2)=[CH:31][C:30]([O:34][CH2:35][CH2:36][N:55]([CH2:56][CH3:57])[CH2:53][CH3:54])=[CH:29][CH:28]=3)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 6341Ethylamine2×HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 575624225-benzyloxy-3-[1-tert-butoxycarbonyl-5-(2-chloro-ethoxy)-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 575624245-benzyloxy-3-[1-tert-butoxycarbonyl-5-(2-diethylaminoethoxy)-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution containing 1.5 g of 5-benzyloxy-3-[1-tert-butoxycarbonyl-5-(2-chloroethoxy)-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester prepared according to procedure J, 1 g of potassium carbonate, 600 mg of potassium iodide and 761 μl of ethylamine in 75 ml of acetonitrile is heated at 80° C. for 18 hours. After this period of time, 1.5 ml of ethylamine are added and the reaction is continued for a further 18 hours at 80° C. This operation is repeated after a further 18 hours and the reaction mixture is then evaporated under reduced pressure. The brown oil obtained is taken up in a mixture of ethyl acetate (80 ml) and of water (80 ml). After separation by settling out and extraction with ethyl acetate (80 ml), the organic extracts are combined, washed with water (100 ml) and with brine (100 ml), dried over magnesium sulfate and then evaporated under reduced pressure to obtain 1.15 g of 5-benzyloxy-3-[1-tert-butoxycarbonyl-5-(2-diethylaminoethoxy)-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester, which is used as it is in the subsequent stage.

Workup

  1. customprepared
  2. waitThis operation is repeated after a further 18 hours
  3. customthe reaction mixture is then evaporated under reduced pressure
  4. customThe brown oil obtained
  5. customAfter separation
  6. extractionextraction with ethyl acetate (80 ml)
  7. washwashed with water (100 ml) and with brine (100 ml)
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-db5a3ddf66794030a8e458f386faa42b
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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