Methanol → racemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-2'-(2-methylphenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1728090Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[N:9][C:10]([O:12][Si](C)(C)C)=[CH2:11].[Br:17][C:18]1[CH:26]=[C:25]2[C:21](/[C:22](=[CH:28]/[C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=3)/[C:23](=[O:27])[NH:24]2)=[CH:20][CH:19]=1.CO>C1(C)C=CC=CC=1>[Br:17][C:18]1[CH:26]=[C:25]2[NH:24][C:23](=[O:27])[C:22]3([CH:28]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=4)[CH2:12][C:10](=[O:11])[NH:9][CH:8]3[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:1])[C:21]2=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 135 °C

Procedure

To a solution of 1-(2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene prepared in example 17a in toluene (20 mL) was added E/Z-6-bromo-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole prepared in example 157a (0.3 g, 0.83 mmol). The reaction mixture was stirred and heated under microwave irradiation in a sealed tube at 135° C. for 0.5 h. After the solution was cooled to room temperature, methanol (50 mL) was added, and then the mixture was concentrated. The residue was purified by chromatography (EtOAc:CH2Cl2=1:3) to give racemic (2′R,3R,4′S)-6-bromo-4′-(3-chlorophenyl)-2′-(2-methylphenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid. (Yield 0.22 g, 53%).

Workup

temperatureAfter the solution was cooled to room temperature
concentrationthe mixture was concentrated
customThe residue was purified by chromatography (EtOAc:CH2Cl2=1:3)

Sources & evidence

ORD record: ord-49e10e9517754749a962895f01d9dd77
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495007B2

Reaction notes

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