4-Tert-Butylaniline → HCID 11233616, compound

HRID 1991475Notes

Reaction equation

HRID 1991475 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([OH:14])=O)[C:6](=[O:15])[CH2:5]2.[C:16]([C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>C(Cl)Cl.CN(C=O)C>[C:16]([C:20]1[CH:21]=[CH:22][C:23]([NH:24][C:12](=[O:14])[CH2:11][N:7]2[C:8]3[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)[CH2:5][C:6]2=[O:15])=[CH:25][CH:26]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 698614-Tert-ButylanilineHCID 13097132HCID 13097132, compoundHCID 178435178HCID 178435178, compound

Product 1

HCID 11233616HCID 11233616, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

In a 1 ml polypropylene vial, 300 μl of a 0.15 M stock solution of (5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)acetic acid 59 in a 1/1 CH2Cl2/DMF mixture were added onto N-dicyclohexyl-N-methyl polystyrene (from Novabiochem, loading: 1.9 mmol/g, 35 mg) and N,N-diisopropyl-methyl-polystyrene (from Argonaut, loading: 3.49 mmol/g, 25.4 mg) followed by 4tertbutyl-aniline (0.044 mmol, 6.6 mg). The reaction mixture was stirred 40 h under vortex and quenched with DMF (400 μl). The suspension was allowed to sediment and the liquid was concentrated under vacuo to afford N-(4-tert-butyl-phenyl)-2-(5-chloro-2-oxo-2,3-dihydro-indol-1-yl)-acetamide 85 (10 mg).

Workup

  1. customquenched with DMF (400 μl)
  2. concentrationthe liquid was concentrated under vacuo

Sources & evidence

ORD record
ord-910bb134d09a4a6cada98b96d262d693
Source dataset
uspto-grants-2010_01
Patent number
US07645887B2

Reaction notes

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