Toluene → 4'-(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1095158Notes

Reaction equation

HRID 1095158 reaction equation
C(OC([N:8]1[C:16]2C(=CC=C(Cl)C=2)/[C:10](=[CH:18]/[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)/[C:9]1=[O:26])=O)(C)(C)C.ClC1C=CC(OC2CCOCC2)=C(C=[N:35]C(O[Si](C)(C)C)=C)C=1.F[C:51](F)(F)[C:52]([OH:54])=O.[C:57]1(C)[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>ClCCl>[Cl:25][C:21]1[CH:20]=[C:19]([CH:18]2[CH2:10][C:9](=[O:26])[NH:8][CH2:16][C:51]32[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[NH:35][C:52]3=[O:54])[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 66640668Z-6-chloro-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl esterHCID 666410081-[5-Chloro-2-(tetrahydro-pyran-4-yloxy)-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene

Product 1

HCID 686290234'-(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a manner similar to the method described in example 32d, E/Z-6-chloro-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester prepared in example 5b (1.3 g, 3.3 mmol) was reacted with 1-[5-chloro-2-(tetrahydro-pyran-4-yloxy)-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene (8.3 mmol) in toluene, then treated with trifluoroacetic acid in dicloromethane to give racemic(2′R, 3R, 4′S)-6-chloro-2′-[5-chloro-2-(tetrahydro-pyran-4-yloxy)-phenyl]]-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 1.2 g, 64%)

Sources & evidence

ORD record
ord-39322ba8316a44489a74a45f31afc176
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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