3-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid methyl ester → Quiflapon

HRID 327221Notes

Reaction equation

HRID 327221 reaction equation
[Cl:1][C:2]1[CH:42]=[CH:41][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[CH:13][CH:14]=3)[C:9]([S:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[C:8]2[CH2:33][C:34]([CH3:40])([CH3:39])[C:35]([O:37]C)=[O:36])=[CH:4][CH:3]=1.COC(=O)C(C)(C)CC1N(CC2C=CC(Cl)=CC=2)C2C(C=1SC(C)(C)C)=CC(OC)=CC=2>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[CH:13][CH:14]=3)[C:9]([S:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[C:8]2[CH2:33][C:34]([CH3:40])([CH3:39])[C:35]([OH:37])=[O:36])=[CH:41][CH:42]=1

Participants

3

Reactant 2

HCID 117625003-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid methyl esterHCID 15225389Methyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-(quinolin-2-ylmethoxy)-1H-indol-2-yl)-2,2-dimethylpropanoate

Product 1

HCID 60923Quiflapon

Procedure

Using the hydrolytic procedure of Step B but substituting the ester of Step D for the ester of Step A provided the title compound, which was recrystallized from 1:1 EtOAc/hexane. m.p. 208° C.

Sources & evidence

ORD record
ord-a450aea2fb6d4df191b25dfd2ad48c2c
Source dataset
uspto-grants-1993_12
Patent number
US05272145

Reaction notes

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