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

HRID 1052284Notes

Reaction equation

HRID 1052284 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.CC1(C)C(C)(C)OB([C:31]2[CH:36]=[CH:35][N:34]=[C:33]([N:37]3[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)[CH:32]=2)O1>>[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:31]3[CH:36]=[CH:35][N:34]=[C:33]([N:37]4[CH2:38][CH2:39][NH:40][CH2:41][CH2:42]4)[CH:32]=3)[NH:22][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 162179482-(1-Piperaziny) pyridine-4-boronic acid pinacol esterHCID 899624376-Bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 730580412-(3,5-Dimethoxyphenethyl)-6-(2-(piperazin-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-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]piperazine (from Aldrich). LCMS calculated for C25H29N6O2 (M+H)+: m/z=445.2. Found 445.2.

Workup

  1. customThe compound was prepared

Sources & evidence

ORD record
ord-508159789fff49fc970209d81cad0ef4
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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