4-[5-[3-Fluoro-5-(trifluoromethoxy)phenyl]-1-(3-pyridyl)pyrazol-3-yl]-2,3-dihydropyrrolo[3,4-c]pyridin-1-one → 4-[1-(3-Chloro-4-fluoro-phenyl)-5-[3-chloro-5-(trifluoromethoxy)phenyl]pyrazol-3-yl]-2,3-dihydropyrrolo[3,4-c]pyridin-1-one

HRID 1771915Notes

Reaction equation

HRID 1771915 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]([C:14]3[CH:19]=[C:18]([O:20][C:21]([F:24])([F:23])[F:22])[CH:17]=[C:16]([Cl:25])[CH:15]=3)=[CH:12][C:11](C(O)=O)=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].FC1C=C(C2N(C3C=NC=CC=3)N=C([C:52]3[C:57]4[CH2:58][NH:59][C:60](=[O:61])[C:56]=4[CH:55]=[CH:54][N:53]=3)C=2)C=C(OC(F)(F)F)C=1.NC1C=CNN=1.BrC1C=CNN=1>>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]([C:14]3[CH:19]=[C:18]([O:20][C:21]([F:22])([F:23])[F:24])[CH:17]=[C:16]([Cl:25])[CH:15]=3)=[CH:12][C:11]([C:52]3[C:57]4[CH2:58][NH:59][C:60](=[O:61])[C:56]=4[CH:55]=[CH:54][N:53]=3)=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 4

HCID 733351184-[5-[3-Fluoro-5-(trifluoromethoxy)phenyl]-1-(3-pyridyl)pyrazol-3-yl]-2,3-dihydropyrrolo[3,4-c]pyridin-1-oneHCID 1182361311-(3-chloro-4-fluorophenyl)-5-(3-chloro-5-trifluoromethoxyphenyl)-1H-pyrazole-3-carboxylic acidHCID 178418806HCID 178418806, compoundHCID 178419412HCID 178419412, compound

Product 1

HCID 733352164-[1-(3-Chloro-4-fluoro-phenyl)-5-[3-chloro-5-(trifluoromethoxy)phenyl]pyrazol-3-yl]-2,3-dihydropyrrolo[3,4-c]pyridin-1-one

Procedure

The synthesis is prepared from 825 mg (1.90 mmol) of the compound from example 9A in a manner analogous to the synthesis of the compound from example 6. This produces 844 mg (81% of theoretical yield) of trimethylsilyl ethyl carbamate (step 1), 541 mg (87% of theoretical yield) of aminopyrazole (step 2) and 223 mg (37% of theoretical yield) of bromopyrazole (step 3). In step 4, 30 mg (27% of theoretical yield) of the title compound are obtained from 100 mg (0.21 mmol) of the compound from step 3.

Sources & evidence

ORD record
ord-e190e0e2140041eb941a6d7627a0470f
Source dataset
uspto-grants-2016_02
Patent number
US09249148B2

Reaction notes

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