Potassium Carbonate → HCID 67125893, compound

HRID 929966Notes

Reaction equation

HRID 929966 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.CC1(C)C(C)(C)OC([C:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH:21]=2)O1.C([O-])([O-])=O.[K+].[K+]>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].CN(C=O)C>[C:29]([O:28][C:26]([N:23]1[CH2:22][CH:21]=[C:20]([C:2]2[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=2)[CH2:25][CH2:24]1)=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 7016458Methyl 5-bromopyridine-2-carboxylateHCID 67125887HCID 67125887, compound

Product 1

HCID 67125893HCID 67125893, compoundYield 68%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
140 °C

Procedure

To a microwave vial was charged with methyl 5-bromopicolinate (250 mg, 1.22 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (393 mg, 1.34 mmol), K2CO3 (400 mg, 3.03 mmol), and 3 mL of DMF. The vial was then flushed with argon while PdCl2(dppf)2 (42 mg, 0.060 mmol) was added. The resulting mixture was then capped and heated at 140° C. for 10 min in a microwave reactor. LC-MS indicated that the reaction was complete. The reaction mixture was then partitioned between EtOAc (25 mL) and water (10 mL). The organic layer was washed with brine (10 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give an oil which was purified by silica gel column chromatography, eluting with 0-60% EtOAc in hexanes, to give methyl 5-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)picolinate (250 mg, 68%). LC-MS (ESI) m/z 319 (M+H)+.

Workup

  1. additionwas added
  2. customThe resulting mixture was then capped
  3. customThe reaction mixture was then partitioned between EtOAc (25 mL) and water (10 mL)
  4. washThe organic layer was washed with brine (10 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give an oil which
  9. customwas purified by silica gel column chromatography
  10. washeluting with 0-60% EtOAc in hexanes

Sources & evidence

ORD record
ord-87d1d3e4bb92475bb4c83f8096108574
Source dataset
uspto-grants-2016_03
Patent number
US09296722B2

Reaction notes

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