1-Methyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)piperazine → 2-(3,5-Dimethoxyphenethyl)-6-(3-(4-methylpiperazin-1-yl)phenyl)-5H-pyrrolo[2,3-b]pyrazine

HRID 1052302Notes

Reaction equation

HRID 1052302 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]=[CH:34][CH:33]=[C:32](B3OC(C)(C)C(C)(C)O3)[CH: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:32]3[CH:33]=[CH:34][CH:35]=[C:30]([N:27]4[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]4)[CH:31]=3)[NH:22][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 592647461-Methyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)piperazineHCID 899624376-Bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 730539612-(3,5-Dimethoxyphenethyl)-6-(3-(4-methylpiperazin-1-yl)phenyl)-5H-pyrrolo[2,3-b]pyrazine

Procedure

The compound was prepared by using procedures 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-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine. LCMS calculated for C27H32N5O3 (M+H)+: m/z=458.3. Found 458.3.

Workup

  1. customThe compound was prepared

Sources & evidence

ORD record
ord-0f72faf299db4472b224be9128de6120
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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