5-Chloro-2,3-dihydro-1H-isoindol-1-one → HCID 178455460, compound

HRID 2277671Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[C:13]([CH3:21])([CH3:20])[O:14][SiH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:7]=1.[Cl:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[C:28](=[O:32])[NH:27][CH2:26]2>>[C:16]([SiH2:15][O:14][C:13]([CH3:21])([CH3:20])[C@@H:9]1[CH2:10][CH2:11][CH2:12][N:8]1[C:6]1[CH:7]=[C:2]([N:27]2[CH2:26][C:25]3[C:29](=[CH:30][CH:31]=[C:23]([Cl:22])[CH:24]=3)[C:28]2=[O:32])[CH:3]=[N:4][CH:5]=1)([CH3:19])([CH3:18])[CH3:17]

Participants

Reactant 2

HCID 197881085-Chloro-2,3-dihydro-1H-isoindol-1-one

HCID 178455458HCID 178455458, compound

Product 1

HCID 178455460HCID 178455460, compound

Procedure

In analogy to the procedures described for the preparation of example 135, 3-bromo-5-[(S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-1-yl]-pyridine (example 135[B]) has been reacted with 5-chloro-2,3-dihydro-isoindol-1-one to give 2-{5-[(S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-1-yl]-pyridin-3-yl}-5-chloro-2,3-dihydro-isoindol-1-one, which was then deprotected with 4M HCl in dioxane to give the title compound as white solid. MS: 344.0 (M+H+).

Sources & evidence

ORD record: ord-e96e49b155d04db3874660d42fec0e6b
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133158B2

Reaction notes

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