N-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → [2-(4-Methylamino-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-(1-methyl-cyclohexyl)-methanone

HRID 1677475

Reaction equation

HRID 1677475 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11]([C:13]3([CH3:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)=[O:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:20][NH:21][C:22]1[CH:27]=[CH:26][C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][CH:23]=1>>[CH3:20][NH:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[N:3]=[C:4]3[C:10]([C:11]([C:13]4([CH3:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]4)=[O:12])=[CH:9][NH:8][C:5]3=[N:6][CH:7]=2)=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 11957892N-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 44199730(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-(1-methyl-cyclohexyl)-methanone

Product 1

HCID 59540838[2-(4-Methylamino-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-(1-methyl-cyclohexyl)-methanone

Procedure

[2-(4-Methylamino-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-(1-methyl-cyclohexyl)-methanone was prepared starting from (2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-(1-methyl-cyclohexyl)-methanone and methyl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amine following general procedures as described in these Examples. MP 273-275° C., M+H=349.

Sources & evidence

ORD record
ord-0634f7bd39f345fe8fe8c42bc1edad90
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Linked notes

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