Sodium Carbonate → HCID 68440792, compound

HRID 2246908Notes

Reaction equation

HRID 2246908 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][C:10](OS(C(F)(F)F)(=O)=O)=[CH:9][CH2:8][N:7]1[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[O:5])[CH3:2].[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][C:10]([C:33]2[CH:34]=[CH:35][C:30]([O:29][CH3:28])=[CH:31][CH:32]=2)=[CH:9][CH2:8][N:7]1[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 433294Lithium ChlorideHCID 86621614HCID 86621614, compound

Product 1

HCID 68440792HCID 68440792, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
75 °C

Procedure

To a suspension of 38.0 g of (S)-1-(4-methoxy-phenyl)-4-trifluoromethanesulfonyloxy-1,2,3,6-tetrahydropyridine-2-carboxylic acid ethyl ester, 18.1 g of 4-methoxyphenylboronic acid, 6.45 g of lithiumchloride in 300 ml of dimethoxyethan are added 100 ml of ethanol, 160 ml of 2N sodium carbonate solution and 2.22 g of tetrakis(triphenylphosphine)palladium. The reaction mixture is heated to 75° C. for 3-6 hours and allowed to cool to room temperature overnight. The reaction mixture is filtered and the filtercake is redissolved in dichloromethane and water. The suspension is filtered again and the organic phase is concentrated under reduced pressure to afford the title compound as a colourless solid. Rf=0.25 (EtOAc-heptane 1:4); Rt=5.00.

Workup

  1. temperatureto cool to room temperature overnight
  2. filtrationThe reaction mixture is filtered
  3. dissolutionthe filtercake is redissolved in dichloromethane
  4. filtrationThe suspension is filtered again
  5. concentrationthe organic phase is concentrated under reduced pressure

Sources & evidence

ORD record
ord-b6e2349b0926448d858560ededb70719
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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