(3-Propoxyphenyl)boronic acid → 2,2-Dimethyl-1-[2-(3-propoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one

HRID 1677443Notes

Reaction equation

HRID 1677443 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH2:17]([O:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)[CH2:18][CH3:19]>CCOC(C)=O>[CH3:13][C:12]([CH3:15])([CH3:14])[C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:25]3[CH:24]=[CH:23][CH:22]=[C:21]([O:20][CH2:17][CH2:18][CH3:19])[CH:26]=3)[N:3]=2)[NH:8][CH:9]=1)=[O:16]

Participants

4

Reactant 2

HCID 3691230(3-Propoxyphenyl)boronic acidHCID 578292181-(2-Bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one

Product 1

HCID 595405362,2-Dimethyl-1-[2-(3-propoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2,2-Dimethyl-1-[2-(3-propoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one was prepared starting from 1-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one and 3-propyloxybenzene boronic acid following general procedures as described in these Examples. Silica gel chromatography using 30-70% EtOAc in hexanes as eluant provided 56 mg (38%) of a yellow solid. MP 179-180° C., M+H=338.

Sources & evidence

ORD record
ord-96c59e75905e43588a7a871d1b23d663
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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