1,2-Dimethoxyethane → 5-bromo-3-(2-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

HRID 1775031Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[N:9][N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:5]2=[CH:6][N:7]=1.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>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>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[F:18])=[N:9][N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:5]2=[CH:6][N:7]=1

Participants

Conditions

Temperature: 145 °C

Procedure

To a microwave tube was added 5-bromo-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine (300 mg, 0.74 mmol), 2-fluorophenylboronic acid (134 mg, 0.96 mmol), Pd(dppf)Cl2(60 mg, 0.07 mmol), sodium carbonate (314 mg, 2.96 mmol), 1,2-dimethoxyethane (3 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 145° C. for 1 hour. The solvent was distilled off and the crude product was purified via flash chromatography eluting with 20% to 95% ethyl acetate in petroleum to afford 5-bromo-3-(2-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine as a yellow oil (105 mg, 38%). ESI MS m/z=377 (M+1).

Workup

customThe tube was flushed with nitrogen for 2 minutes
distillationThe solvent was distilled off
customthe crude product was purified via flash chromatography
washeluting with 20% to 95% ethyl acetate in petroleum

Sources & evidence

ORD record: ord-e19b2e0ceaf144e58102be7d7f109f09
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260425B2

Reaction notes

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