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

HRID 1774983Notes

Reaction equation

HRID 1774983 reaction equation
[N:1]1[CH:6]=[C:5](B(O)O)[CH:4]=[N:3][CH:2]=1.Br[C:11]1[CH:12]=[C:13]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:18][N:17](C3CCCCO3)[C:14]2=[CH:15][N:16]=1>>[C:20]1([C:19]2[C:13]3[C:14](=[CH:15][N:16]=[C:11]([C:5]4[CH:6]=[N:1][CH:2]=[N:3][CH:4]=4)[CH:12]=3)[NH:17][N:18]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 866766845-bromo-3-phenyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 712539083-phenyl-5-(pyrimidin-5-yl)-1H-pyrazolo[3,4-c]pyridineYield 25%

Procedure

Following the procedures in Example 136, pyrimidin-5-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 150 as a yellow solid (25 mg, 25%) over two steps. 1H NMR (400 MHz, DMSO) δ 9.59 (s, 1H), 9.26 (s, 1H), 9.21 (s, 1H), 8.79 (s, 1H), 8.40 (s, 1H), 8.18 (d, 2H), 7.57 (t, 2H), 7.47 (t, 1H). ESI MS m/z=274 (M+1)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-977c97870662492d985d534c597dffce
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

Loading…