1-(2-Allyloxy-5-iodo-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene → 2'-(2-Allyloxy-5-iodo-phenyl)-6-chloro-4'-(3-chlorophenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

HRID 1174059Notes

Reaction equation

HRID 1174059 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:20]/[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)/[C:7](=[O:19])[N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si](C)(C)C)=[CH:4][CH:3]=1.[CH2:28]([O:31][C:32]1[CH:37]=[CH:36][C:35]([I:38])=[CH:34][C:33]=1[CH:39]=[N:40][C:41]([O:43][Si:44]([CH3:47])([CH3:46])[CH3:45])=[CH2:42])[CH:29]=[CH2:30]>C1(C)C=CC=CC=1>[CH2:28]([O:31][C:32]1[CH:37]=[CH:36][C:35]([I:38])=[CH:34][C:33]=1[CH:39]1[C:6]2([C:5]3[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=3)[NH:8][C:7]2=[O:19])[CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)[CH2:42][C:41](=[O:43])[NH:40]1)[CH:29]=[CH2:30].[CH3:11][O:12][CH:13]([Si:44]([CH3:45])([CH3:46])[CH3:47])[CH3:14]

Participants

4

Reactant 2

HCID 723257941-(2-Allyloxy-5-iodo-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 86615089Z-6-chloro-3-(3-chloro-benzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indole-2-one

Product 1

HCID 777001692'-(2-Allyloxy-5-iodo-phenyl)-6-chloro-4'-(3-chlorophenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilaneYield 44.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to the method described in example 1d, E/Z-6-chloro-3-(3-chlorobenzylidene)-1-(2-trimethylsilanyl-ethoxymethyl-1,3-dihydro-indole-2-one (6 g, 15 mmol) prepared in example 1b was reacted with 1-(2-allyloxy-5-iodo-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (26 g, 65 mmol) prepared in example 18b in toluene (100 mL) to give racemic (2′R, 3R, 4′S)-2′-(2-allyloxy-5-iodo-phenyl)-6-chloro-4′-(3-chlorophenyl)-2,3-dihydro-2,6′-dioxo spiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane as a white foam (5 g, 44%)

Sources & evidence

ORD record
ord-716689704a4144f2ae6b0c6316882f24
Source dataset
uspto-grants-2010_11
Patent number
US07834179B2

Reaction notes

Loading…