4-Chlorophenyl Isocyanate → 3-(3,4-Dimethoxy-phenyl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid (4-chloro-phenyl)-amide

HRID 1820884Notes

Reaction equation

HRID 1820884 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1>C1C=CC=CC=1.O1CCCC1.CN(C)C1C=CN=CC=1>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([N:13]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:19]3[C:11]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:12]2)=[O:29])=[CH:23][CH:22]=1

Participants

6

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 116732853-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 578917063-(3,4-Dimethoxy-phenyl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid (4-chloro-phenyl)-amideYield 40%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
200 °C

Procedure

3-(3,4-Dimethoxy-phenyl)-1H-pyrrolo-[2,3-b]pyridine 1 (40 mg, 0.16 mmol) was dissolved in benzene and 4-chlorophenyl isocyanate (36 mg, 0.24 mol) dissolved in tetrahydrofuran (4 mL) was added. 4-Dimethylaminopyridine (20 mg, polymer bound) was added. The reaction was heated in a CEM Discover microwave at 200° C. for 10 minutes. The mixture was filtered and concentrated. The resulting solid was washed with a minimum of methanol, filtered, and then washed with dichloromethane to provide 26, (26 mg, 40%). MS(ESI) [M+H+]+=408.4.

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. washThe resulting solid was washed with a minimum of methanol
  5. filtrationfiltered
  6. washwashed with dichloromethane

Sources & evidence

ORD record
ord-e5917b7dd6cc4d92b0244fbf9485412b
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

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