3-Fluoro-4-(methylcarbamoyl)benzeneboronic acid → 4-(2-(3,5-Dimethoxyphenethyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)-2-fluoro-N-methylbenzamide

HRID 1052277Notes

Reaction equation

HRID 1052277 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.[F:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][C:29]=1[C:30](=[O:33])[NH:31][CH3:32]>>[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:26]3[CH:27]=[CH:28][C:29]([C:30]([NH:31][CH3:32])=[O:33])=[C:24]([F:23])[CH:25]=3)[NH:22][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 447174673-Fluoro-4-(methylcarbamoyl)benzeneboronic acidHCID 899624376-Bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 730574664-(2-(3,5-Dimethoxyphenethyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)-2-fluoro-N-methylbenzamide

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 3-fluoro-4-(methylcarbamoyl)phenylboronic acid (from Combi-Blocks). LCMS calculated for C24H24FN4O3 (M+H)+: m/z=435.2. Found 435.2.

Workup

  1. customThe compound was prepared

Sources & evidence

ORD record
ord-b585a6464ef14665a58e8c6669ffdfce
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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