1-(Tetrahydro-2H-pyran-2-YL)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-imidazole → 5-(1H-imidazol-5-yl)-3-phenyl-1H-pyrazolo[3,4-c]pyridine

HRID 1775023Notes

Reaction equation

HRID 1775023 reaction equation
O1CCCCC1[N:7]1[C:11](B2OC(C)(C)C(C)(C)O2)=[CH:10][N:9]=[CH:8]1.Br[C:22]1[CH:23]=[C:24]2[C:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[N:29][N:28](C3CCCCO3)[C:25]2=[CH:26][N:27]=1>>[NH:7]1[C:11]([C:22]2[CH:23]=[C:24]3[C:30]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[N:29][NH:28][C:25]3=[CH:26][N:27]=2)=[CH:10][N:9]=[CH:8]1

Participants

3

Reactant 2

HCID 248800081-(Tetrahydro-2H-pyran-2-YL)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-imidazoleHCID 866766845-bromo-3-phenyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 712536615-(1H-imidazol-5-yl)-3-phenyl-1H-pyrazolo[3,4-c]pyridineYield 25%

Procedure

Following the procedures in Example 204, 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazole 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 213 as a yellow solid (30 mg, 25%) over two steps. 1H NMR (400 MHz, DMSO) δ 8.23 (s, 1H), 7.75 (s, 1H), 7.43 (m, 1H), 7.34 (m, 1H), 7.27 (m, 2H), 6.77 (m, 2H), 6.66 (m, 1H). ESI MS m/z=262 (M+1)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-9b9d237dce2f4e2387e22b2700fb396f
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

Loading…