Piperidine → HCID 58181278, compound

HRID 1961437Notes

Reaction equation

HRID 1961437 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[NH:52]1[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]1>COCCOC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:52]1([C:2]2[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=2)[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 62657Potassium Phosphate, TribasicHCID 8171545-Bromopyridine-2-carbonitrileHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

Product 1

HCID 58181278HCID 58181278, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 500 mg (2.73 mmol) 5-bromopicolinonitrile, 63 mg (0.07 mmol) Pd2 dba3 and 130 mg (0.27 mmol) 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl in 20 ml DME was stirred and degassed with N2 for 10 min. 1.45 g (6.83 mmol) K3PO4 and 297 μl (3.0 mmol) piperidine were added. The mixture was heated at 80° C. under N2 over night. The mixture was cooled to r.t. and filtered through a plug of SiO2 with CH2Cl2/MeOH 9:1. The filtrate was concentrated and purified by flash chromatography (SiO2, Pet. ether/EtOAc 4:1→1:1) to afford 323 mg (63%, yellow oil).

Workup

  1. customdegassed with N2 for 10 min
  2. temperatureThe mixture was cooled to r.t.
  3. filtrationfiltered through a plug of SiO2 with CH2Cl2/MeOH 9:1
  4. concentrationThe filtrate was concentrated
  5. custompurified by flash chromatography (SiO2, Pet. ether/EtOAc 4:1→1:1)
  6. customto afford 323 mg (63%, yellow oil)

Sources & evidence

ORD record
ord-22009cc7c9da4329ab05c405c95cd959
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

Loading…