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

HRID 1095153Notes

Reaction equation

HRID 1095153 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(F)=CC(OC2CCOCC2)=C(C=[N:35]C(O[Si](C)(C)C)=C)C=1.F[C:52](F)(F)[C:53]([OH:55])=O.[C:58]1(C)[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=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:52]32[C:63]2[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=2)[NH:35][C:53]3=[O:55])[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 666415601-[5-Chloro-4-fluoro-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 50%

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 (0.79 g, 2 mmol) was reacted with 1-[5-chloro-4-fluoro-2-(tetrahydro-pyran-4-yloxy)-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene (5 mmol) in toluene, then treated with trifluoroacetic acid in dicloromethane to give racemic(2′R, 3R, 4′S)-6-chloro-2′-[5-chloro-4-fluoro-2-(tetrahydro-pyran-4-yloxy)-phenyl]]-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.59 g, 50%)

Sources & evidence

ORD record
ord-78ec09cee5a4434a96e129bc95a9eee7
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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