4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbonitrile → 4-(2-(3,5-Dimethoxyphenethyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)picolinonitrile

HRID 1052280Notes

Reaction equation

HRID 1052280 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]([C:37]#[N:38])[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]([C:37]#[N:38])[CH:32]=3)[NH:22][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 457862934-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbonitrileHCID 899624376-Bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 730577604-(2-(3,5-Dimethoxyphenethyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)picolinonitrile

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 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbonitrile (from Combi-Blocks). LCMS calculated for C22H20N5O2(M+H)+: m/z=386.2. Found 386.2.

Workup

  1. customThe compound was prepared

Sources & evidence

ORD record
ord-698b356893d145deae3941084fce4513
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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