Water → Benzyl 2-methoxy-3',6'-dihydro-3,4'-bipyridine-1'(2'H)-carboxylate

HRID 1664805Notes

Reaction equation

HRID 1664805 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].FC(F)(F)S(O[C:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:17][CH:18]=1)(=O)=O.[CH3:31][O:32][C:33]1[C:38](B(O)O)=[CH:37][CH:36]=[CH:35][N:34]=1.O>CN(C)C=O.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[CH3:31][O:32][C:33]1[C:38]([C:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:17][CH:18]=2)=[CH:37][CH:36]=[CH:35][N:34]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 11303044benzyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 67439388Benzyl 2-methoxy-3',6'-dihydro-3,4'-bipyridine-1'(2'H)-carboxylateYield 72.8%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Sodium carbonate (2.0 M in water; 4.0 mL, 8.09 mmol) was added to a solution of benzyl 4-{[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-1(2H)-carboxylate (1.26 g, 3.45 mmol) and (2-methoxypyridin-3-yl)boronic acid (0.58 g, 3.79 mmol) in N,N-dimethylformamide (12 mL). Dichloro [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.25 g, 0.345 mmol) was added and the mixture was heated to 70° C. After 2 h, the mixture was cooled to ambient temperature and water was added. The mixture was extracted with ethyl acetate and the combined organic extracts were dried over magnesium sulfate and concentrated. Purification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate) to give the title compound (0.815 g). MS 325.2 (M+1).

Workup

  1. temperaturethe mixture was cooled to ambient temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe combined organic extracts were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-8fef8faa2e7b4d648dd17cd31fa09e64
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

Loading…