Z-6-chloro-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester → HCID 178515582, compound

HRID 1095152Notes

Reaction equation

HRID 1095152 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl: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([Si](C)(C)[O:32][C@H:33]1[CH2:38][CH2:37][C@H:36]([O:39][C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][C:41]=2[CH:47]=[N:48][C:49]([O:51][Si](C)(C)C)=[CH2:50])[CH2:35][CH2:34]1)(C)(C)C>C1(C)C=CC=CC=1>[Cl: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)[CH2:51][C:49](=[O:50])[NH:48][CH:47]3[C:41]3[CH:42]=[C:43]([Cl:46])[CH:44]=[CH:45][C:40]=3[O:39][C@H:36]3[CH2:35][CH2:34][C@@H:33]([OH:32])[CH2:38][CH2:37]3)[C:11]2=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 66640668Z-6-chloro-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl esterHCID 178463709HCID 178463709, compound

Product 1

HCID 178515582HCID 178515582, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to the method described in example 1e, E/Z-6-chloro-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester prepared in example 1b (0.47 g, 1.2 mmol) was reacted 1-[2-[trans-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyloxy]-5-chloro-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene (3 mmol) in toluene to give racemic(2′R, 3R, 4′S)-6-chloro-2′-[5-chloro-2-(cis-4-hydroxy-cyclohexyloxy)-phenyl]-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a pale yellow solid (Yield 0.3 g, 42%)

Sources & evidence

ORD record
ord-56a6626aa07d4c18a3f9371cf1d54b63
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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