Acetic Acid → 4-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-benzoic acid

HRID 1677463Notes

Reaction equation

HRID 1677463 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.[C:17]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)([OH:19])=[O:18].CC(O)=O>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:23]3[CH:24]=[CH:25][C:20]([C:17]([OH:19])=[O:18])=[CH:21][CH:22]=3)[N:3]=2)[NH:8][CH:9]=1)=[O:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3121834-Carboxyphenylboronic AcidHCID 578292181-(2-Bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one

Product 1

HCID 595410734-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-benzoic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-benzoic acid was prepared starting from 1-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one and 4-carboxyphenylboronic acid following general procedures as described in these Examples. Silica gel chromatography using 50-100% [5% AcOH:EtOAc]/Hexanes as eluant gave 10 mg (6%) of a pale brown solid. M+H=324.

Sources & evidence

ORD record
ord-d6b7e4d436ff4e66ad968e953f20c150
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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