Water → HCID 10727356, compound

HRID 594237Notes

Reaction equation

HRID 594237 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].C[Sn](C)(C)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.O.CCOC(C)=O>C1(C)C=CC=C(C)C=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:8][O:7][C:5]([C:4]1[CH:9]=[CH:10][N:11]=[C:2]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:3]=1)=[O:6]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2736842Methyl 2-chloropyridine-4-carboxylateHCID 11021057Pyridine, 2-(trimethylstannyl)-

Product 1

HCID 10727356HCID 10727356, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 7929M-XyleneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of commercially available methyl 2-chloroisonicotinate (300 mg; 1.74 mmol), 2-(trimethylstannyl)pyridine (422 mg; 1.74 mmol), and PdCl2(PPh3)2 (122 mg; 0.17 mmol) in anh. meta-xylene (7 ml) was heated to 75° C., under nitrogen, for 18 h. After cooling to rt, water and AcOEt were added. The separated aq. layer was further extracted with AcOEt. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=15/1) afforded methyl[2,2′-bipyridine]-4-carboxylate as a yellow solid. LC-MS (conditions A): tR=0.46 min.; [M+H]+: 215.15 g/mol.

Workup

  1. temperatureAfter cooling to rt
  2. extractionThe separated aq. layer was further extracted with AcOEt
  3. washThe mixed organic layers were washed with brine
  4. dry with materialdried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification by FC (DCM/MeOH=15/1)

Sources & evidence

ORD record
ord-43a05ae9256742eca6e72a41733143fc
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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