2-Fluoro-5-(trifluoromethyl)phenyl isocyanate → HCID 57445292, compound

HRID 550896Notes

Reaction equation

HRID 550896 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]([NH2:19])=[O:18])=[CH:4][CH:3]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=1[N:31]=[C:32]=[O:33]>O1CCCC1>[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=1[NH:31][C:32](=[O:33])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]([NH2:19])=[O:18])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 574453543-(4-aminophenyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

Product 1

HCID 57445292HCID 57445292, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 130 mg of 3-(4-aminophenyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamide in 5 mL of tetrahydrofuran are added dropwise 85 μL of 2-fluoro-5-(trifluoromethyl)phenyl isocyanate. The reaction mixture is then stirred for 16 hours at room temperature under an argon atmosphere and then concentrated under reduced pressure. The residue obtained is chromatographed on a column of silica (eluent: 9/1 dichloromethane/methanol by volume). The fractions containing the expected product are concentrated under reduced pressure. 237 mg of 3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-1H-pyrrolo[2,3-b]pyridine-2-carboxamide are obtained in the form of a white solid, the characteristics of which are as follows:

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. customis chromatographed on a column of silica (eluent: 9/1 dichloromethane/methanol by volume)
  4. additionThe fractions containing the expected product
  5. concentrationare concentrated under reduced pressure

Sources & evidence

ORD record
ord-63c7c314ba2947e4853b330b5d4445b5
Source dataset
uspto-grants-2011_05
Patent number
US07947706B2

Reaction notes

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