Imidazole → HCID 68841301, compound

HRID 1726056Notes

Reaction equation

HRID 1726056 reaction equation
N1C=CN=C1.[C:6]1([P:12](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:21]([O:25][C:26]([N:28]1[C:36]2[C:31](=[CH:32][C:33]([OH:37])=[CH:34][CH:35]=2)[C:30]([CH:38]2[CH2:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[N:39]2[C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[N:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]>ClCCl>[C:21]([O:25][C:26]([N:28]1[C:36]2[C:31](=[CH:32][C:33]([O:37][P:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[O:13])=[CH:34][CH:35]=2)[C:30]([CH:38]2[CH2:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[N:39]2[C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[N:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 73910Diphenylphosphinic chlorideHCID 68840193HCID 68840193, compound

Product 1

HCID 68841301HCID 68841301, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

90 mg of imidazole and 250 μl of diphenylphosphinyl chloride are added to a solution of 140 mg of 3-(1-tert-butoxycarbonyl-2,3-dihydro-1H-indol-2-yl)-5-hydroxyindazole-1-carboxylic acid tert-butyl ester in 15 ml of dichloromethane. The reaction medium is stirred at ambient temperature overnight. After dilution with 10 ml of dichloromethane and 10 ml of distilled water, the medium is separated by settling out. The organic phase is dried over magnesium sulfate, filtered, and concentrated under reduced pressure in a rotary evaporator. The crude is taken up in a dichloromethane/methanol mixture and the solid is filtered off. After concentration under reduced pressure, the filtrate is purified by flash chromatography, eluent: cyclohexane/ethyl acetate 8:2 to obtain 200 mg of 3-(1-tert-butoxycarbonyl-2,3-dihydro-1H-indol-2-yl)-5-(diphenylphosphinoyloxy)indazole-1-carboxylic acid tert-butyl ester.

Workup

  1. customAfter dilution with 10 ml of dichloromethane and 10 ml of distilled water, the medium is separated
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure in a rotary evaporator
  5. filtrationthe solid is filtered off
  6. concentrationAfter concentration under reduced pressure
  7. customthe filtrate is purified by flash chromatography, eluent

Sources & evidence

ORD record
ord-c921cfd841f4465caf4e17a21a35fcc4
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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