2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)pyrazine → 3-phenyl-5-(pyrazin-2-yl)-1H-pyrazolo[3,4-c]pyridine

HRID 1775024Notes

Reaction equation

HRID 1775024 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[N:13][CH:12]=[CH:11][N:10]=2)O1.Br[C:17]1[CH:18]=[C:19]2[C:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:24][N:23](C3CCCCO3)[C:20]2=[CH:21][N:22]=1>>[C:26]1([C:25]2[C:19]3[C:20](=[CH:21][N:22]=[C:17]([C:9]4[CH:14]=[N:13][CH:12]=[CH:11][N:10]=4)[CH:18]=3)[NH:23][N:24]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 177504772-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)pyrazineHCID 866766845-bromo-3-phenyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 712535243-phenyl-5-(pyrazin-2-yl)-1H-pyrazolo[3,4-c]pyridineYield 28%

Procedure

Following the procedures in Example 204, 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazine and 5-bromo-3-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine were reacted and the product was deprotected to give 214 as a yellow solid (22 mg, 28%) over two steps. 1H NMR (400 MHz, DMSO) δ 9.61 (s, 1H), 9.26 (s, 1H), 8.97 (s, 1H), 8.76 (s, 1H), 8.67 (d, 1H), 8.05 (t, 2H), 7.61 (t, 2H), 7.48 (t, 1H). ESI MS m/z=274 (M+1)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-af265f4360034d8297adf5659d61b784
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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