3-(Dimethylcarbamoyl)-4-fluorobenzeneboronic acid → 5-(2-(3,5-Dimethoxyphenethyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)-2-fluoro-N,N-dimethylbenzamide

HRID 1052274Notes

Reaction equation

HRID 1052274 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]([CH3:37])[C:25]([C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][C:32]=1[F:33])=[O:26]>>[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:30]=[CH:31][C:32]([F:33])=[C:27]([CH:28]=3)[C:25]([N:24]([CH3:37])[CH3:23])=[O:26])[NH:22][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 447175423-(Dimethylcarbamoyl)-4-fluorobenzeneboronic acidHCID 899624376-Bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 730574625-(2-(3,5-Dimethoxyphenethyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)-2-fluoro-N,N-dimethylbenzamide

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 3-(dimethylcarbamoyl)-4-fluorophenylboronic acid (from Combi-Blocks). LCMS calculated for C25H26FN4O3 (M+H)+: m/z=449.2. Found 449.1.

Workup

  1. customThe compound was prepared

Sources & evidence

ORD record
ord-e1eabe94d8e64bd9a5949412753b8847
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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