Acetonitrile → 5-(pyridin-3-yl)-3-(pyridin-4-yl)-1H-pyrazolo[3,4-c]pyridine

HRID 1775018Notes

Reaction equation

I[C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[CH:9]=2)[NH:4][N:3]=1.[N:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].CC#N>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O.C(O)C.COCCOC>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:8]2[CH:9]=[C:10]3[C:2]([C:20]4[CH:21]=[CH:22][N:17]=[CH:18][CH:19]=4)=[N:3][NH:4][C:5]3=[CH:6][N:7]=2)[CH:12]=1

Participants

Conditions

Temperature: 160 °C

Procedure

To a microwave tube was added 3-iodo-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine from Example 4 (100 mg, 0.31 mmol), pyridin-4-ylboronic acid (190 mg, 1.55 mmol), Pd(dppf)Cl2 (50 mg, 0.06 mmol), sodium carbonate (131 mg, 1.24 mmol), 1,2-dimethoxyethane (2 mL), ethanol (0.3 mL) and water (0.3 mL). The tube was flushed with nitrogen for 2 minutes and heated in a Biotage microwave at 160° C. for 1 hour. The solvent was distilled off and the crude product was purified via reverse phase HPLC eluting with 15% CH3CN aqueous 10 mmol NH4HCO3 solution to afford 194 as a white solid (18 mg, 21%). 1H NMR (400 MHz, DMSO) 1H NMR (500 MHz, DMSO) δ 9.44 (s, 1H), 9.28 (s, 1H), 8.76-8.73 (m, 3H), 8.62-8.59 (m, 2H), 8.19 (d, J=6.0 Hz, 2H), 7.55-7.53 (m, 1H). ESI MS m/z=274 (M+1)

Workup

customThe tube was flushed with nitrogen for 2 minutes
distillationThe solvent was distilled off
customthe crude product was purified via reverse phase HPLC

Sources & evidence

ORD record: ord-e6a4a528b545426fb0ec699e8c27f353
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260425B2

Reaction notes

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