Triethylamine → HCID 68600114, compound

HRID 2196429Notes

Reaction equation

HRID 2196429 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]1[C:13]([Sn](CCCC)(CCCC)CCCC)=[CH:12][N:11]=[N:10]1.Br[C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1.[F-].[K+]>C1(C)C=CC=CC=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.CO>[CH3:8][N:9]1[C:13]([C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=2)=[CH:12][N:11]=[N:10]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 12081Methyl 4-bromobenzoateHCID 522689Potassium FluorideHCID 226098261-methyl-5-(tributylstannyl)-1H-1,2,3-triazole

Product 1

HCID 68600114HCID 68600114, compoundYield 115.1%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Triethylamine (0.28 ml, 2.00 mmol) was added to a mixture of 1-methyl-5-(tributylstannanyl)-1H-1,2,3-triazole (781 mg, 2.1 mmol), methyl 4-bromobenzoate (430 mg, 2.0 mmol), and BIS(TRIPHENYLPHOSPHINE)PALLADIUM(II) CHLORIDE (70.2 mg, 0.10 mmol) in toluene (10 ml) to give a yellow suspension. The reaction mixture was purged with N2, sealed and stirred at 100° C. for 3 hr. Potassium fluoride (465 mg, 8.00 mmol) and MeOH (2 mL) were added. The mixture was stirred at RT for 2 h, filtered on celite, and rinsed with EtOAc. The combined filtrates were concentrated and the residue was purified on a 25M biotage column to give 0.5 g of methyl 4-(1-methyl-1H-1,2,3-triazol-5-yl)benzoate as a tan solid.

Workup

  1. customto give a yellow suspension
  2. customThe reaction mixture was purged with N2
  3. customsealed
  4. stirringThe mixture was stirred at RT for 2 h
  5. filtrationfiltered on celite
  6. washrinsed with EtOAc
  7. concentrationThe combined filtrates were concentrated
  8. customthe residue was purified on a 25M biotage column

Sources & evidence

ORD record
ord-da5351559dbb415390ad4754cacfd39d
Source dataset
uspto-grants-2012_12
Patent number
US08338434B2

Reaction notes

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