3-(3-HYDROXYPROPYL)PHENYLBORONIC ACID → 1-{2-[3-(3-Hydroxy-propyl)-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one

HRID 1677447Notes

Reaction equation

HRID 1677447 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.[OH:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1>CCOC(C)=O>[OH:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[C:25]([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:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 36721733-(3-HYDROXYPROPYL)PHENYLBORONIC ACIDHCID 578292181-(2-Bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one

Product 1

HCID 595410081-{2-[3-(3-Hydroxy-propyl)-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-(3-Hydroxy-propyl)-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-(3-hydroxypropyl)benzeneboronic acid following general procedures as described in these Examples. Silica gel chromatography using 20-100% EtOAc in hexanes as eluant provided 80 mg (48%) of a yellow solid. MP 170-171° C., M+H=338.

Sources & evidence

ORD record
ord-da01b746fed6484497ffd295c6f404cb
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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