B-[3-(2-Methylpropoxy)phenyl]boronic acid → 1-[2-(3-Isobutoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one

HRID 1677441Notes

Reaction equation

HRID 1677441 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:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)[CH:18]([CH3:20])[CH3:19]>CCOC(C)=O>[CH2:17]([O:21][C:22]1[CH:27]=[C:26]([C:2]2[N:3]=[C:4]3[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][NH:8][C:5]3=[N:6][CH:7]=2)[CH:25]=[CH:24][CH:23]=1)[CH:18]([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 16217826B-[3-(2-Methylpropoxy)phenyl]boronic acidHCID 578292181-(2-Bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one

Product 1

HCID 595410101-[2-(3-Isobutoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-[2-(3-Isobutoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-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-Isobutoxyphenylboronic acid following general procedures as described in these Examples. Silica gel chromatography using 30-100% EtOAc in hexanes as eluant provided 170 mg (94%) of a pale yellow solid. MP 177-178° C., M+H=351.

Sources & evidence

ORD record
ord-4af7dc5d66164bb1b46e0ba72da866ae
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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