Potassium Carbonate → HCID 21105684, compound

HRID 2426693Notes

Reaction equation

HRID 2426693 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:17]2[CH2:18][CH2:19][N:20]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:21][CH:22]=2)O1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.ClCCl.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]>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:17]2[CH2:22][CH2:21][N:20]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19][CH:18]=2)=[N:3][CH:4]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 8170982-Bromo-5-chloropyridineHCID 21105682HCID 21105682, compound

Product 1

HCID 21105684HCID 21105684, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-bromo-5-chloropyridine (131 mg) in DMF (degassed with nitrogen; 4.5 ml) was added to a mixture of tert-butyl 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridin-1-carbamate (Eastwood, Paul R., Tetrahedron Lett, 41, 19, 2000, 3705-3708; 200 mg), potassium carbonate (0.265 g) and Pd(dppf)Cl2 (50 mg). The mixture was heated at 80° C. for 8 hours. After cooling, the mixture was diluted with dichloromethane and washed with sodium carbonate solution and water. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography (silica gel, mobile phase: heptane/ethyl acetate (2%)/dichloromethane (5%), later heptane/ethyl acetate (5%)/dichloromethane (5%).

Workup

  1. temperatureAfter cooling
  2. washwashed with sodium carbonate solution and water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (silica gel, mobile phase

Sources & evidence

ORD record
ord-ad908934ec1a4512a7a0521323a7c20c
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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