Dichloromethane → 6-chloro-4'-(3-chlorophenyl)-2'-(1-methylene-propyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1728074Notes

Reaction equation

HRID 1728074 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:20]/[C:21]3[CH:26]=[C:25](F)[CH:24]=[C:23](F)[CH:22]=3)/[C:7](=[O:19])[N:8]2COCC[Si](C)(C)C)=[CH:4][CH:3]=1.[CH2:29]=[C:30]([CH:33]=[N:34][C:35]([O:37][Si](C)(C)C)=[CH2:36])[CH2:31][CH3:32].FC(F)(F)C(O)=O.C(N(C(C)C)CC)(C)C.[Cl:58]CCl>C1(C)C=CC=CC=1.CO>[Cl:1][C:2]1[CH:10]=[C:9]2[NH:8][C:7](=[O:19])[C:6]3([CH:20]([C:21]4[CH:22]=[CH:23][CH:24]=[C:25]([Cl:58])[CH:26]=4)[CH2:36][C:35](=[O:37])[NH:34][CH:33]3[C:30](=[CH2:29])[CH2:31][CH3:32])[C:5]2=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 76567901HCID 76567901, compoundHCID 131727336Z-6-Chloro-3-(3,5-difluoro-benzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indol-2-one

Product 1

HCID 775802116-chloro-4'-(3-chlorophenyl)-2'-(1-methylene-propyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

In a manner similar to the method described in example 97a, 55d, E/Z-6-Chloro-3-(3,5-difluoro-benzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indol-2-one (0.21 g, 0.5 mmol) prepared in example 133a was reacted with 1-(1-methylene-propyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (1 g, 5.25 mmol) prepared in example 80a in toluene, then treated with trifluoroacetic acid (5 ml) in dichloromethane, followed by treatment with diisopropylethylamine (1 mL) in methanol to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(1-methylene-propyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (35 mg, 18% for two steps).

Sources & evidence

ORD record
ord-c08bdab7d9b4480da267ef55441abe9b
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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