Toluene → HCID 66844924, compound

HRID 253124Notes

Reaction equation

HRID 253124 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7](OS(C(F)(F)F)(=O)=O)[C:8](=[O:15])[N:9]2[C:13]=1[CH2:12][CH2:11][CH:10]2[CH3:14])=[O:4].[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>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.CCO>[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:7]1[C:8](=[O:15])[N:9]2[C:13](=[C:5]([C:3]([OH:2])=[O:4])[CH:6]=1)[CH2:12][CH2:11][CH:10]2[CH3:14]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 86614017HCID 86614017, compound

Product 1

HCID 66844924HCID 66844924, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

To a microwave tube was added methyl-3-methyl-5-oxo-6-(trifluoromethylsulfonyloxy)-1,2,3,5-tetrahydroindolizine-8-carboxylate (94 mg, 0.26 mmol), 2-fluorophenylboronic acid (37 mg, 0.26 mmol, Aldrich), and 2 M sodium carbonate (0.65 mL, 1.30 mmol). To this was added 4 mL of toluene, 0.25 mL of EtOH, and Pd(PPh3)4 (20 mg, 0.17 mmol, Aldrich). The tube was sealed and treated in Emry's optimizer for 15 min at 160° C. The aqueous phase was separated and acidified to pH 2 with 2 N HCl and extracted with EtOAc (3×). The combined EtOAc layers were washed with brine, dried over MgSO4, and concentrated in vacuo to give 40 mg (53%) of the title compound as a light brown residue. MS m/z: 288.1(M+1).

Workup

  1. customThe tube was sealed
  2. additiontreated in Emry's optimizer for 15 min at 160° C
  3. customThe aqueous phase was separated
  4. extractionextracted with EtOAc (3×)
  5. washThe combined EtOAc layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a81f4b0bd48c4523b1efcab3a448e13b
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

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