4-(bromomethyl)-3-methyl-5-phenylisoxazole → tert-butyl [5-chloro-1'-[(3-methyl-5-phenylisoxazol-4-yl)methyl]-2,5'-dioxospiro[indole-3,3'-pyrrolidin]-1(2H)-yl]acetate

HRID 883656Notes

Reaction equation

HRID 883656 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][C:13](=[O:15])[N:12](CC4C=CC=CC=4F)[CH2:11]3)[C:9](=[O:24])[N:8]([CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:5]2=[CH:6][CH:7]=1.Br[CH2:34][C:35]1[C:36]([CH3:46])=[N:37][O:38][C:39]=1[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][C:13](=[O:15])[N:12]([CH2:34][C:35]4[C:36]([CH3:46])=[N:37][O:38][C:39]=4[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[CH2:11]3)[C:9](=[O:24])[N:8]([CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:5]2=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 27765184-(bromomethyl)-3-methyl-5-phenylisoxazoleHCID 58017127tert-butyl [5-chloro-1'-(2-fluorobenzyl)-2,5'-dioxospiro[indole-3,3'-pyrrolidin]-1(2H)-yl]acetate2×

Product 1

HCID 24827316tert-butyl [5-chloro-1'-[(3-methyl-5-phenylisoxazol-4-yl)methyl]-2,5'-dioxospiro[indole-3,3'-pyrrolidin]-1(2H)-yl]acetateYield 53%

Procedure

Following the general method as outlined for Intermediate 33, starting from tert-butyl (5-chloro-2,5′-dioxospiro[indole-3,3′-pyrrolidin]-1(2H)-yl)acetate (intermediate 32) and 4-(bromomethyl)-3-methyl-5-phenylisoxazole, the title compound was isolated, after purification by chromatography (silica) eluting with cyclohexane containing increasing amounts of ethyl acetate (10 to 50%), as a white solid in 53% yield (HPLC purity 89%). MS (ESI+): 522.4; MS (ESI−):520.1

Sources & evidence

ORD record
ord-9c1f811e0b5a4e08bb5de3eb84ddebff
Source dataset
uspto-grants-2012_08
Patent number
US08236963B2

Reaction notes

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