5-Chloro-2,3-dihydro-1H-isoindol-1-one → HCID 86685965, compound

HRID 2277673Notes

Reaction equation

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

Participants

Reactant 2

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

HCID 86685966HCID 86685966, compound

Product 1

HCID 86685965HCID 86685965, compound

Procedure

In analogy to the procedures described for the preparation of example 137, 3-bromo-5-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-1-yl]-pyridine (example 137 [B]) has been reacted with 5-chloro-2,3-dihydro-isoindol-1-one to give 2-{5-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-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 light yellow solid. MS: 330.1 (M+H+).

Sources & evidence

ORD record: ord-7815536cefec4aae969cc723b5536a65
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133158B2

Reaction notes

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