4-Bromoisoindolin-1-one → 4-[1-(3-Chloro-4-fluoro-phenyl)-5-(3-chloro-5-fluoro-phenyl)pyrazol-3-yl]isoindolin-1-one

HRID 1771912Notes

Reaction equation

HRID 1771912 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]([C:14]3[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([Cl:21])[CH:15]=3)=[CH:12][C:11](C3C4CNC(=O)C=4C=CN=3)=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].ClC1C2CNC(=O)C=2C=CN=1.Br[C:44]1[CH:52]=[CH:51][CH:50]=[C:49]2[C:45]=1[CH2:46][NH:47][C:48]2=[O:53]>>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]([C:14]3[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([Cl:21])[CH:15]=3)=[CH:12][C:11]([C:44]3[CH:52]=[CH:51][CH:50]=[C:49]4[C:45]=3[CH2:46][NH:47][C:48]4=[O:53])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 3

HCID 219075094-Bromoisoindolin-1-oneHCID 733351144-[1-(3-Chloro-4-fluoro-phenyl)-5-(3-chloro-5-fluoro-phenyl)pyrazol-3-yl]-2,3-dihydropyrrolo[3,4-c]pyridin-1-oneHCID 825978324-chloro-1H,2H,3H-pyrrolo[3,4-c]pyridin-1-one

Product 1

HCID 865788304-[1-(3-Chloro-4-fluoro-phenyl)-5-(3-chloro-5-fluoro-phenyl)pyrazol-3-yl]isoindolin-1-one

Procedure

The synthesis of the title compound is performed starting from 100 mg (0.25 mmol) of the product from step 3 of example 1 in a manner analogous to the synthesis of the compound from example 1. In step 4, instead of the compound from example 22A, 4-bromo-2,3-dihydroisoindol-1-on (63 mg, 0.30 mmol) is used. The result is 74 mg (65% of theoretical yield) of the title compound.

Sources & evidence

ORD record
ord-5ded4bc17ac44eb9a04eb098bce167ec
Source dataset
uspto-grants-2016_02
Patent number
US09249148B2

Reaction notes

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