Trifluoroacetic acid → HCID 76568131, compound

HRID 1728110Notes

Reaction equation

HRID 1728110 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Br:17])[CH:15]=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.[C:27]([CH:30]=[N:31][C:32]([O:34][Si](C)(C)C)=[CH2:33])([CH3:29])=[CH2:28].FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[Br:17][C:14]1[CH:15]=[C:16]2[NH:8][C:9](=[O:26])[C:10]3([CH:18]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=4)[CH2:33][C:32](=[O:34])[NH:31][CH:30]3[C:27]([CH3:29])=[CH2:28])[C:11]2=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 765681151-Isopropenyl-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 86615102HCID 86615102, compound

Product 1

HCID 76568131HCID 76568131, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to the method described in example 41b, E/Z-6-bromo-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (5 g, 12.8 mmol) prepared in example 172a was reacted with 1-isopropenyl-3-trimethylsilyoxy-2-aza-1,3-butadiene prepared in example 87b in toluene, then treated with trifluoroacetic acid to give racemic (2′R,3R,4′S)-6-bromo-4′-(3-chlorophenyl)-2′-isopropenylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a yellow solid (Yield 2.2 g, 40%).

Sources & evidence

ORD record
ord-bea4be5e0df649439e569946d27b88dc
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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