3,4,5-Trimethoxybenzeneboronic acid → (1-Methyl-cyclopentyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone

HRID 1677451Notes

Reaction equation

HRID 1677451 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11]([C:13]3([CH3:18])[CH2:17][CH2:16][CH2:15][CH2:14]3)=[O:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28]>CCOC(C)=O>[CH3:18][C:13]1([C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([C:23]4[CH:24]=[C:25]([O:29][CH3:30])[C:26]([O:27][CH3:28])=[C:21]([O:20][CH3:19])[CH:22]=4)[N:3]=3)[NH:8][CH:9]=2)=[O:12])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 44199843(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-(1-methyl-cyclopentyl)-methanone

Product 1

HCID 59540658(1-Methyl-cyclopentyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(1-Methyl-cyclopentyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone was prepared starting from (2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-(1-methyl-cyclopentyl)-methanone and 3,4,5-trimethoxyphenylboronic acid following general procedures as described in these Examples. Silica gel chromatography using 2-50% EtOAc in hexanes as eluant gave a pale brown solid which was washed with 1:1 Et2O/Hexanes provided 10 mg (7.7%) of an off white solid. MP 244-246° C., M+H=396.

Workup

  1. customgave a pale brown solid which
  2. washwas washed with 1:1 Et2O/Hexanes
  3. customprovided 10 mg (7.7%) of an off white solid

Sources & evidence

ORD record
ord-3b5d60cd2ae6472b837b07f5eaa128b7
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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