Dimethylformamide → HCID 86730348, compound

HRID 1427047Notes

Reaction equation

HRID 1427047 reaction equation
CN(C)C=O.[C:6]([N:13]1[CH2:18][CH:17]=[C:16](B2OC(C)(C)C(C)(C)O2)[CH2:15][CH2:14]1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].Cl[C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][N:30]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N:30]1[CH:31]=[C:32]([C:33]([O:35][CH3:36])=[O:34])[CH:37]=[CH:38][C:29]=1[C:16]1[CH2:15][CH2:14][N:13]([C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7])[CH2:18][CH:17]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 86730348HCID 86730348, compoundYield 22.3%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

N,N-dimethylformamide (100 mL) was added to commercially available 1-N—BOC-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine (4.68 g, 15.1 mmol), commercially available methyl 6-chloronicotinate (2.81 g, 16.4 mmol), 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) (1.17 g, 1.60 mmol), and potassium carbonate (7.02 g, 50.8 mmol). The reaction liquid was stirred under nitrogen atmosphere at 100° C. for 2 hours. The reaction liquid was allowed to stand to cool to room temperature and then diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed serially with a dilute aqueous ammonia solution and a saturated saline solution, and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the filtrate was concentrated under vacuum. The residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=9:1-1:1) to obtain the title compound (1.07 g, 22%).

Workup

  1. customThe reaction liquid
  2. customThe reaction liquid
  3. temperatureto cool to room temperature
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layer was washed serially with a dilute aqueous ammonia solution
  6. dry with materiala saturated saline solution, and then dried over anhydrous sodium sulfate
  7. customThe drying agent was separated by filtration
  8. concentrationthe filtrate was concentrated under vacuum
  9. customThe residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=9:1-1:1)

Sources & evidence

ORD record
ord-6034a69b67024c90aa8ae84f87c47a8a
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

Loading…