4-Fluorophenyl isocyanate → HCID 57298450, compound

HRID 1739585Notes

Reaction equation

HRID 1739585 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.[F:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1>CN(C)C1C=CN=CC=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:34](=[O:35])[NH:33][C:30]3[CH:31]=[CH:32][C:27]([F:26])=[CH:28][CH:29]=3)[CH:12]=2)=[C:6]([O:23][CH3:24])[CH:5]=1

Participants

5

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 114732633-(2-Methoxy-4-methoxycarboxybenzyl)-5-nitroindole

Product 1

HCID 57298450HCID 57298450, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-[5-nitro-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester (1.30 grams, 3.82 mmol) and 4-dimethylaminopyridine (0.58 mL, 4.77 mmol) in methylene chloride (60 mL) was added 4-fluorophenylisocyanate (0.70 mL, 5.73 mmol). The resulting solution was stirred for 18 hours, at room temperature, and then diluted with methylene chloride. The solution was washed with 1 M hydrochloric acid, water and brine, then dried over magnesium sulfate. Concentration in vacuo followed by trituration in diethylether gave 4-[1-(4-fluoro-phenylcarbamoyl)-5-nitro-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester (1.60 grams, 88% yield).

Workup

  1. washThe solution was washed with 1 M hydrochloric acid, water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-7e76783e15fe4de1be0bc4dcdd8cb0fa
Source dataset
uspto-grants-1999_10
Patent number
US05965745

Reaction notes

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