2-(4-Methylpiperazin-1-yl)pyridine-4-boronic acid, pinacol ester → 6-(2,6-Difluoro-3,5-dimethoxyphenyl)-3-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]-1H-pyrazolo[4,3-c]pyridine

HRID 1778689Notes

Reaction equation

HRID 1778689 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[C:13]1[N:18]=[CH:17][C:16]2[C:19](I)=[N:20][NH:21][C:15]=2[CH:14]=1.[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[C:34](B3OC(C)(C)C(C)(C)O3)[CH:33]=[CH:32][N:31]=2)[CH2:26][CH2:25]1>>[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[C:13]1[N:18]=[CH:17][C:16]2[C:19]([C:34]3[CH:33]=[CH:32][N:31]=[C:30]([N:27]4[CH2:26][CH2:25][N:24]([CH3:23])[CH2:29][CH2:28]4)[CH:35]=3)=[N:20][NH:21][C:15]=2[CH:14]=1

Participants

3

Reactant 2

HCID 27695372-(4-Methylpiperazin-1-yl)pyridine-4-boronic acid, pinacol esterHCID 1784934906-(2,6-difluoro-3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 762853306-(2,6-Difluoro-3,5-dimethoxyphenyl)-3-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]-1H-pyrazolo[4,3-c]pyridine

Procedure

This compound was prepared by using procedures analogous to those described for the synthesis of Example 4, Step 2 starting from 6-(2,6-difluoro-3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[4,3-c]pyridine and 1-methyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]piperazine. LCMS (M+H)+=467.2.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-6d8de6c923714c858154365ed411547c
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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