(3-(5-Methyl-1,3,4-oxadiazol-2-yl)phenyl)boronic acid → (1-Methyl-cyclohexyl)-{2-[3-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-methanone

HRID 1677459Notes

Reaction equation

HRID 1677459 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][C:21]1[O:25][C:24]([C:26]2[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=2)=[N:23][N:22]=1>>[CH3:19][C:13]1([C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([C:28]4[CH:29]=[CH:30][CH:31]=[C:26]([C:24]5[O:25][C:21]([CH3:20])=[N:22][N:23]=5)[CH:27]=4)[N:3]=3)[NH:8][CH:9]=2)=[O:12])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 44119380(3-(5-Methyl-1,3,4-oxadiazol-2-yl)phenyl)boronic acidHCID 44199730(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-(1-methyl-cyclohexyl)-methanone

Product 1

HCID 59540696(1-Methyl-cyclohexyl)-{2-[3-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-methanone

Procedure

(1-Methyl-cyclohexyl)-{2-[3-(5-methyl-[1,3,4]oxadiazol-2-yl)-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-cyclohexyl)-methanone and 3-(5-Methyl-1,3,4-oxadiazol-2-yl)phenylboronic acid following general procedures as described in these Examples. MP 234-236° C., M+H=402.

Sources & evidence

ORD record
ord-037c0e5e41144cfbb44417326a963d73
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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