6-Chloro-2-picoline → HCID 57507761, compound

HRID 605796Notes

Reaction equation

HRID 605796 reaction equation
CC(C)([O-])C.[Na+].Cl[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=1.[NH:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][CH2:23][CH:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]2)[CH2:17][CH2:16]1>CCOC(C)=O.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].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>[CH3:14][C:10]1[N:9]=[C:8]([N:15]2[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][CH2:23][CH:24]3[CH2:25][CH2:26][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:28][CH2:29]3)[CH2:17][CH2:16]2)[CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 876016-Chloro-2-picolineHCID 23676156Sodium t-butoxideHCID 57421831HCID 57421831, compound

Product 1

HCID 57507761HCID 57507761, compoundYield 91.4%

Reagents, catalysts & solvents 3

HCID 27342162-(Dicyclohexylphosphino)biphenylCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

In an argon atmosphere, sodium tert-butoxide, (0.52 g), tris(dibenzylideneacetone)dipalladium (100 mg) and 2-(dicyclohexylphosphino)biphenyl (76 mg) were added to a Tol (22 ml) solution of 2-chloro-6-methylpyridine (0.56 g) and tert-butyl 4-[3-(4-piperidinyl)propyl]-1-piperidinecarboxylate (1.1 g), followed by heating with stirring at 100° C. for 1 hour. This was cooled to room temperature, diluted with EtOAc, and washed with aqueous saturated sodium hydrogencarbonate solution. This was dried over anhydrous magnesium sulfate, the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=10:1 (v/v)) to obtain tert-butyl 4-{3-[1-(6-methyl-2-pyridinyl)-4-piperidyl]propyl}-1-piperidinecarboxylate (1.3 g).

Workup

  1. temperatureby heating
  2. temperatureThis was cooled to room temperature
  3. washwashed with aqueous saturated sodium hydrogencarbonate solution
  4. dry with materialThis was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=10:1 (v/v))

Sources & evidence

ORD record
ord-457187bb4e8a423a855019c5f187b403
Source dataset
uspto-grants-2011_03
Patent number
US07915261B2

Reaction notes

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