Trifluoroacetic acid → 5-[6-(2,6-Difluoro-3,5-dimethoxyphenyl)-1H-pyrazolo[4,3-c]pyridin-3-yl]-N,N-dimethyl-2,3-dihydro-1-benzofuran-2-carboxamide

HRID 1778785Notes

Reaction equation

HRID 1778785 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([O:17][CH3:18])=[C:11]([F:19])[C:10]=1[C:20]1[N:25]=[CH:24][C:23]2[C:26](I)=[N:27][N:28](C3CCCCO3)[C:22]=2[CH:21]=1.[CH3:36][N:37]([CH3:58])[C:38]([CH:40]1[CH2:44][C:43]2[CH:45]=[C:46](B3OC(C)(C)C(C)(C)O3)[CH:47]=[CH:48][C:42]=2[O:41]1)=[O:39]>>[F:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([O:17][CH3:18])=[C:11]([F:19])[C:10]=1[C:20]1[N:25]=[CH:24][C:23]2[C:26]([C:46]3[CH:47]=[CH:48][C:42]4[O:41][CH:40]([C:38]([N:37]([CH3:36])[CH3:58])=[O:39])[CH2:44][C:43]=4[CH:45]=3)=[N:27][NH:28][C:22]=2[CH:21]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 86722799N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamideHCID 86722838HCID 86722838, compound

Product 1

HCID 762850685-[6-(2,6-Difluoro-3,5-dimethoxyphenyl)-1H-pyrazolo[4,3-c]pyridin-3-yl]-N,N-dimethyl-2,3-dihydro-1-benzofuran-2-carboxamide

Procedure

This compound was prepared as a TFA salt by using procedures analogous to those described for the synthesis of Example 83 starting from 6-(2,6-difluoro-3,5-dimethoxyphenyl)-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine (Example 52, Step 5) and N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide (Peak II from chiral separation, Example 4, Step 1). LCMS (M+H)+=481.0.

Sources & evidence

ORD record
ord-850babad809547b19b706025c2fc2fae
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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