HCID 86715492, compound → HCID 86715491, compound

HRID 2284582Notes

Reaction equation

HRID 2284582 reaction equation
[C:1]1([C:6]2[CH:7]=[C:8]([C:12]3[C:17]([C:18]4[CH:19]=[C:20]5[CH:26]=[N:25][NH:24][C:21]5=[N:22][CH:23]=4)=[CH:16][CH:15]=[CH:14][N:13]=3)[CH:9]=[CH:10][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1>CCO.[Pd]>[CH:1]1([C:6]2[CH:7]=[C:8]([C:12]3[C:17]([C:18]4[CH:19]=[C:20]5[CH:26]=[N:25][NH:24][C:21]5=[N:22][CH:23]=4)=[CH:16][CH:15]=[CH:14][N:13]=3)[CH:9]=[CH:10][CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 86715492HCID 86715492, compound

Product 1

HCID 86715491HCID 86715491, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-(2-(3-cyclopentenylphenyl)pyridin-3-yl)-1H-pyrazolo[3,4-b]pyridine (130 mg) was hydrogenated with Pd/C (15 mg) in EtOH (15 mL) over a period of 10 h under balloon H2 after degassing and back filling the flask with the hydrogen. The reaction mixture was filtered through celite and purified by preparative HPLC to provide 5-(2-(3-cyclopentylphenyl)pyridin-3-yl)-1H-pyrazolo[3,4-b]pyridine as a white solid. 1H NMR (DMSO-d6): δ 8.84 (d, 1H, J=4.7 Hz), 8.41 (d, 1H, J=7.9 Hz), 8.16 (app s, 2H), 8.14 (app s, 1H), 7.89 (app t, 1H, J=7.5 Hz), 7.23 (app s, 2H), 7.22-7.20 (m, 1H), 7.08 (s, 1H), 2.80 (q, 1H, J=8.2 Hz), 1.75-1.68 (m, 2H), 1.48-1.39 (m, 4H), 1.17-1.07 (m, 2H).LCMS: rt 5.13 min (A), purity 97%, MS (m/e) 341 (MH+).

Workup

  1. customafter degassing
  2. filtrationThe reaction mixture was filtered through celite
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-8f5f160ec0f54a3a8b6696574f9b9bd9
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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