1-Methylindazole-5-boronic acid pinacol ester → 2-(3,5-Dimethoxyphenethyl)-6-(1-methyl-1H-indazol-5-yl)-5H-pyrrolo[2,3-b]pyrazine

HRID 1052282Notes

Reaction equation

HRID 1052282 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[C:32]2[C:27](=[CH:28][C:29](B3OC(C)(C)C(C)(C)O3)=[CH:30][CH:31]=2)[CH:26]=[N: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:29]3[CH:28]=[C:27]4[C:32](=[CH:31][CH:30]=3)[N:24]([CH3:23])[N:25]=[CH:26]4)[NH:22][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 469415731-Methylindazole-5-boronic acid pinacol esterHCID 899624376-Bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 730577622-(3,5-Dimethoxyphenethyl)-6-(1-methyl-1H-indazol-5-yl)-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-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (from Combi-Blocks). LCMS calculated for C24H24N5O2(M+H)+: m/z=414.2. Found 414.2.

Workup

  1. customThe compound was prepared

Sources & evidence

ORD record
ord-1f0e85155ba841039b3189a6173fd8db
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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