Toluene → 4-[1-(benzhydryl-carbamoyl)-5-nitro-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester

HRID 1739580Notes

Reaction equation

HRID 1739580 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=3)[NH:13][CH:12]=2)=[C:6]([O:23][CH3:24])[CH:5]=1.C(N(CC)CC)C.[C:33](Cl)(Cl)=[O:34].C1(C)C=CC=CC=1.Cl.[NH2:45][CH:46]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=3)[N:13]([C:33](=[O:34])[NH:45][CH:46]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[CH:12]=2)=[C:6]([O:23][CH3:24])[CH:5]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 6371PhosgeneHCID 8471TriethylamineHCID 78921Benzhydrylammonium chlorideHCID 114732633-(2-Methoxy-4-methoxycarboxybenzyl)-5-nitroindole

Product 1

HCID 536387694-[1-(benzhydryl-carbamoyl)-5-nitro-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylesterYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[5-nitro-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester (0.50 grams, 1.47 mmol) and triethylamine (0.62 mL, 4.41 mmol) in methylene chloride (30 mL), at 0° C., was added a solution of phosgene in toluene (1.9 M in toluene, 1.5 mL, 2.9 mmol). The solution was warmed to room temperature and stirred for 1 hour. To this was added aminodiphenylmethane hydrochloride (0.65 grams, 2.94 mmol) and the resulting solution was stirred for 12 hours at room temperature. The solution was concentrated in vacuo and the crude triturated with methanol. The resulting pale yellow solid was collected via filtration to give 4-[1-(benzhydryl-carbamoyl)-5-nitro-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester (0.672 grams, 83% yield).

Workup

  1. stirringthe resulting solution was stirred for 12 hours at room temperature
  2. concentrationThe solution was concentrated in vacuo
  3. customthe crude triturated with methanol
  4. filtrationThe resulting pale yellow solid was collected via filtration

Sources & evidence

ORD record
ord-8daa3074f5ed419e8d29338ef07fe594
Source dataset
uspto-grants-1999_10
Patent number
US05965745

Reaction notes

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