Piperidine → HCID 68276037, compound

HRID 1475933Notes

Reaction equation

HRID 1475933 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:10](/[CH:11]=[CH:12]/[CH:13]=O)=[C:4]2[CH:3]=1.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl-].[NH4+]>ClCCCl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[C:10](/[CH:11]=[CH:12]/[CH2:13][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[C:4]2[CH:3]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 25517Ammonium ChlorideHCID 5049666Sodium triacetoxyborohydrideHCID 86711216HCID 86711216, compound

Product 1

HCID 68276037HCID 68276037, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of (E)-3-(5-bromo-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)acrylaldehyde (385 mg, 1.1 mmol) and piperidine (160 μL, 1.6 mmol) in 1,2-dichloroethane (5 mL) was added sodium triacetoxyborohydride (340 mg, 1.6 mmol). The mixture and stirred at r.t for 2.5 h and a saturated solution of ammonium chloride (10 mL) was added. The separated aqueous layer was then extracted with dichloromethane (3×25 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to afford a residue which was purified by automated flash-chromatography (methanol/dichloromethane; 15/85). The title compound was obtained as a bright yellow solid (354 mg, 77%). LCMS m/z 426.1; 428.1 (weak) (M+H)+341.0; 343.0 (strong), ret time=2.15 min.

Workup

  1. extractionThe separated aqueous layer was then extracted with dichloromethane (3×25 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford a residue which
  7. customwas purified by automated flash-chromatography (methanol/dichloromethane; 15/85)

Sources & evidence

ORD record
ord-611ad22872cb4787a091244bd4601e3a
Source dataset
uspto-grants-2015_04
Patent number
US09018395B2

Reaction notes

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