Pyrrolidine → HCID 68960388, compound

HRID 1728197Notes

Reaction equation

HRID 1728197 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[C:6]([CH:9]=1)[CH:7]=O.[Cl:16][C:17]1[CH:25]=[C:24]2[C:20]([CH2:21][C:22](=[O:26])[NH:23]2)=[CH:19][CH:18]=1.N1CCCC1>CO>[Cl:16][C:17]1[CH:25]=[C:24]2[C:20]([C:21](=[CH:7][C:6]3[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[O:10][CH2:11][C:12]([F:15])([F:14])[F:13])[C:22](=[O:26])[NH:23]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 47709505-Chloro-2-(2,2,2-trifluoroethoxy)benzaldehyde

Product 1

HCID 68960388HCID 68960388, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

5-Chloro-2-(2,2,2-trifluoro-ethoxy)-benzaldehyde (4 g, 16 mmol) and 6-chlorooxindole (2.8 g, 16 mmol) were mixed in anhydrous methanol (20 mL). Then pyrrolidine (1.32 mL, 16 mmol) was added slowly at r.t. The mixture was heated to 70° C. for 3 h and cooled to room temperature. The precipitate was collected by filtration to give title compound as a yellow solid (Yield: 4.45 g, 72%).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-ffc311f32b0c417d8a6fb93816b50742
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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