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

HRID 1677467Notes

Reaction equation

HRID 1677467 reaction equation
[C:1]12([C:11]([C:13]3[C:21]4[C:16](=[N:17][CH:18]=[C:19](Br)[N:20]=4)[NH:15][CH:14]=3)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:23][O:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32]>>[C:1]12([C:11]([C:13]3[C:21]4[C:16](=[N:17][CH:18]=[C:19]([C:27]5[CH:28]=[C:29]([O:33][CH3:34])[C:30]([O:31][CH3:32])=[C:25]([O:24][CH3:23])[CH:26]=5)[N:20]=4)[NH:15][CH:14]=3)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

3

Reactant 2

HCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 44182410Adamantan-1-yl-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-methanone

Product 1

HCID 59540589Adamantan-1-yl-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone

Procedure

Adamantan-1-yl-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone was prepared starting from adamantan-1-yl-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-methanone and 3,4,5-trimethoxyphenylboronic acid following general procedures as described in these Examples. MP 267-268° C., M+H=448.

Sources & evidence

ORD record
ord-ff731fd7c2084a288740385c3a572fd6
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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