2-(Bromomethyl)-4-chloro-1-fluorobenzene → tert-butyl [5-chloro-1'-(5-chloro-2-fluorobenzyl)-2,5'-dioxospiro[indole-3,3'-pyrrolidin]-1(2H)-yl]acetate

HRID 883655Notes

Reaction equation

HRID 883655 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][C:13](=[O:15])[N:12]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[F:23])[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.[Cl:33]C1C=CC(F)=C(C=1)CBr>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][C:13](=[O:15])[N:12]([CH2:16][C:17]4[CH:22]=[C:21]([Cl:33])[CH:20]=[CH:19][C:18]=4[F:23])[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 27736262-(Bromomethyl)-4-chloro-1-fluorobenzeneHCID 58017127tert-butyl [5-chloro-1'-(2-fluorobenzyl)-2,5'-dioxospiro[indole-3,3'-pyrrolidin]-1(2H)-yl]acetate2×

Product 1

HCID 24828874tert-butyl [5-chloro-1'-(5-chloro-2-fluorobenzyl)-2,5'-dioxospiro[indole-3,3'-pyrrolidin]-1(2H)-yl]acetateYield 72.7%

Procedure

Following the general method as outlined for Intermediate 33, starting from tert-butyl [5-chloro-1′-(2-fluorobenzyl)-2,5′-dioxospiro[indole-3,3′-pyrrolidin]-1(2H)-yl]acetate (intermediate 32) and 5-chloro-2-fluorobenzyl bromide, the title compound was isolated, after purification by chromatography (silica) eluting with cyclohexane containing increasing amounts of ethyl acetate (5 to 40%), as a white solid in 72.7% yield (HPLC purity 94%). MS (ESI+): 493.4; MS (ESI−): 491.0

Sources & evidence

ORD record
ord-69cadbac370a43749d174faf6a9537e3
Source dataset
uspto-grants-2012_08
Patent number
US08236963B2

Reaction notes

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