HCID 18789608, compound → HCID 69352075, compound

HRID 1106769Notes

Reaction equation

HRID 1106769 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:33]=[CH:34][CH:35]=1)[O:7][CH2:8][C:9]1[N:10]=[CH:11][N:12]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=1)([O-])=O>C(OCC)(=O)C.C(O)C.[Pd]>[C:14]([N:12]1[CH:13]=[C:9]([CH2:8][O:7][C:6]2[CH:5]=[C:4]([NH2:1])[CH:35]=[CH:34][CH:33]=2)[N:10]=[CH:11]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 1

HCID 18789608HCID 18789608, compound

Product 1

HCID 69352075HCID 69352075, compoundYield 42.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(3-nitro-phenoxymethyl)-1-trityl-1H-imidazole (1.5 g, from above) and 10% Pd/C (0.18 g) in ethyl acetate (60 mL) and ethanol(30 mL) was hydrogenated at 1 atmosphere overnight. The reaction mixture was filtered through a celite pad and the filtrate was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with ethyl acetate:hexane (40:60) to afford 3-(1-trityl-1H-imidazol-4-ylmethoxy)phenylamine (0.6 g).

Workup

  1. customwas hydrogenated at 1 atmosphere overnight
  2. filtrationThe reaction mixture was filtered through a celite pad
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by flash column chromatography on silica gel eluting with ethyl acetate:hexane (40:60)

Sources & evidence

ORD record
ord-d929903e10f54c749514fc15014dc4dd
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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