2-(4-Methylpiperazin-1-yl)pyridine-4-boronic acid, pinacol ester → 2-(3,5-Dimethoxyphenethyl)-6-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazine

HRID 1052275Notes

Reaction equation

HRID 1052275 reaction equation
Br[C:2]1[NH:22][C:5]2=[N:6][CH:7]=[C:8]([CH2:10][CH2:11][C:12]3[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[CH:13]=3)[N:9]=[C:4]2[CH:3]=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>>[CH3:21][O:20][C:14]1[CH:13]=[C:12]([CH:17]=[C:16]([O:18][CH3:19])[CH:15]=1)[CH2:11][CH2:10][C:8]1[N:9]=[C:4]2[CH:3]=[C:2]([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)[NH:22][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 27695372-(4-Methylpiperazin-1-yl)pyridine-4-boronic acid, pinacol esterHCID 899624376-Bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 730574652-(3,5-Dimethoxyphenethyl)-6-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazine

Procedure

The compound was prepared by using procedure analogous to those described for the synthesis of Example 53, Step 2 starting from 6-bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazine and 1-methyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]piperazine (from Boron Molecular). LCMS calculated for C26H31N6O2 (M+H)+: m/z=459.2. Found 459.1.

Workup

  1. customThe compound was prepared

Sources & evidence

ORD record
ord-56481bbe9b8b480fbabbf5283923e335
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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