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

Participants

Role	Name	HCID	Charge
Reactant	4-(bromomethyl)-3-methyl-5-phenylisoxazole	HCID 2776518	—
Reactant	tert-butyl [5-chloro-1'-(2-fluorobenzyl)-2,5'-dioxospiro[indole-3,3'-pyrrolidin]-1(2H)-yl]acetate	HCID 58017127	—
Product	tert-butyl [5-chloro-1'-[(3-methyl-5-phenylisoxazol-4-yl)methyl]-2,5'-dioxospiro[indole-3,3'-pyrrolidin]-1(2H)-yl]acetate	HCID 24827316	53%

Reaction Steps

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

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08236963B2
Source dataset	uspto-grants-2012_08
ORD ID	ord-9c1f811e0b5a4e08bb5de3eb84ddebff
Source note	uspto-grants-2012_08