Piperidine → 5-Bromo-2-(4-methoxyphenyl)-3-(2-(piperidin-1-yl)ethyl)pyrazolo[1,5-a]pyridine

HRID 1475959Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:10]([CH2:11][CH:12]=O)=[C:4]2[CH:3]=1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:10]([CH2:11][CH2:12][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[C:4]2[CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 2-(5-bromo-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)acetaldehyde (40 mg, 0.12 mmol) and piperidine (23 μl, 0.23 mmol) in 1,2-dichloroethane (3.5 ml) was added sodium triacetoxyborohydride (49 m, 0.23 mmol). The reaction mixture was stirred at 20° C. for 17 h. The reaction mixture was diluted with dichloromethane (10 mL) and washed with a 5% sodium bicarbonate solution (6 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a residue that was purified by automated ISCO chromatography (methanol/dichloromethane; 5/95). The title compound was obtained as a white solid (28 mg, 58%). LCMS m/z 414.1, 416.1 (M+H)+, ret. time=1.76 min.

Workup

washwashed with a 5% sodium bicarbonate solution (6 mL)
dry with materialThe organic layer was dried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give a residue that
customwas purified by automated ISCO chromatography (methanol/dichloromethane; 5/95)

Sources & evidence

ORD record: ord-392d71b87d474121b878c55e1036574e
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018395B2

Reaction notes

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