1H-Pyrazole-4-boronic acid → 3-phenyl-5-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine

HRID 1774976Notes

Reaction equation

HRID 1774976 reaction equation
[NH:1]1[CH:5]=[C:4](B(O)O)[CH:3]=[N:2]1.Br[C:10]1[CH:11]=[C:12]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:17][N:16](C3CCCCO3)[C:13]2=[CH:14][N:15]=1>>[C:19]1([C:18]2[C:12]3[C:13](=[CH:14][N:15]=[C:10]([C:4]4[CH:5]=[N:1][NH:2][CH:3]=4)[CH:11]=3)[NH:16][N:17]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 177502781H-Pyrazole-4-boronic acidHCID 866766845-bromo-3-phenyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 712538403-phenyl-5-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridineYield 23%

Procedure

Following the procedures as described in Example 136, 1H-pyrazol-4-ylboronic acid 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 137 as a yellow solid (26 mg, 23%) over two steps. 1H NMR (400 MHz, DMSO) δ 12.9 (s, 1H), 9.05 (s, 1H), 8.37-8.09 (m, 5H), 7.56 (m, 1H), 7.44 (m, 1H)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-c80d839627aa46fdba6472fd160fe5a0
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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