4-Bromoisoindolin-1-one → 4-[5-[3-Fluoro-5-(trifluoromethoxy)phenyl]-1-(3-pyridyl)pyrazol-3-yl]isoindolin-1-one

HRID 1771913Notes

Reaction equation

HRID 1771913 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:13]2[N:17]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[N:16]=[C:15]([C:24]3[C:29]4[CH2:30][NH:31][C:32](=[O:33])[C:28]=4[CH:27]=[CH:26]N=3)[CH:14]=2)[CH:5]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:7]=1.Cl[C:35]1C2CNC(=O)C=2C=CN=1.BrC1C=CC=C2C=1CNC2=O>>[F:1][C:2]1[CH:3]=[C:4]([C:13]2[N:17]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[N:16]=[C:15]([C:24]3[CH:35]=[CH:26][CH:27]=[C:28]4[C:29]=3[CH2:30][NH:31][C:32]4=[O:33])[CH:14]=2)[CH:5]=[C:6]([O:8][C:9]([F:12])([F:10])[F:11])[CH:7]=1

Participants

4

Reactant 3

HCID 219075094-Bromoisoindolin-1-oneHCID 733351184-[5-[3-Fluoro-5-(trifluoromethoxy)phenyl]-1-(3-pyridyl)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 733351194-[5-[3-Fluoro-5-(trifluoromethoxy)phenyl]-1-(3-pyridyl)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 the compound from example 6 in a manner analogous to step 4 from example 6, whereby instead of the compound from example 22A, 4-bromo-2,3-dihydroisoindole-1-on (63 mg, 0.30 mmol) is used. This produces 64 mg (56% of theoretical yield) of the title compound.

Sources & evidence

ORD record
ord-6f22522bd23841cbb8655d5e0d62d96d
Source dataset
uspto-grants-2016_02
Patent number
US09249148B2

Reaction notes

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