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Pyrrolidine → Z-4-[4-chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester

HRID 504465
Notes
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Reaction equation

HRID 504465 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[CH:33]=O)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].N1CCCC1>CO>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2/[CH:33]=[C:6]2\[C:7](=[O:11])[NH:8][C:9]3[C:5]\2=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=3)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 577501934-(4-Chloro-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86632056Z-4-[4-chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl esterYield 40.9%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 6-chlorooxindole (0.84 g, 5 mmol) and 4-(4-chloro-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (1.7 g, 5 mmol) in methanol (10 mL) was added pyrrolidine (0.4 mL, 5 mmol) dropwise. The mixture was then heated at 70° C. for 3 h. After cooled to 4° C., the mixture was filtered and the precipitate was collected, dried to give the title compound as a bright yellow solid (1 g).

Workup

  1. temperatureAfter cooled to 4° C.
  2. filtrationthe mixture was filtered
  3. customthe precipitate was collected
  4. customdried

Sources & evidence

ORD record
ord-a7c47a1a22b549aabdc68b7ce0339f4c
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07776875B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes