Triethylamine → Tetrabutylammonium Fluoride

HRID 2035722Notes

Reaction equation

HRID 2035722 reaction equation
C(N([CH2:6][CH3:7])CC)C.Br[C:9]1[CH:14]=CN=[C:11](C)[CH:10]=1.C([Si](C#CC1N=NN([CH:30]2[CH2:36][CH2:35]C3C=[CH:38][CH:39]=[CH:40][C:33]=3[N:32]([CH2:41][C:42](F)(F)[F:43])[C:31]2=O)C=1)(CC)CC)C>C1(P([Pd](Cl)(Cl)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I.CN(C=O)C>[CH3:14][CH2:9][CH2:10][CH2:11][N+:32]([CH2:31][CH2:30][CH2:36][CH3:35])([CH2:33][CH2:40][CH2:39][CH3:38])[CH2:41][CH2:42][CH2:6][CH3:7].[F-:43]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27628354-Bromo-2-methylpyridineHCID 66683835HCID 66683835, compound

Product 1

HCID 2724141Tetrabutylammonium Fluoride

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178479802HCID 178479802, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Triethyl amine (0.030 ml, 0.213 mmol), 4-bromo-2-methylpyridine (19 mg, 0.111 mmol), bis(triphenylphosphino)palladium dichloride (6 mg, 8.55 μmol), and DMF (2 ml) were added to the 25-mL flask containing the crude 3-(4-Ethynyl-1,2,3-triazol-1-yl)-1-(2,2,2-trifluoro-ethyl)-1,3,4,5-tetrahydro-1-benzazepin-2-one and the resulting brownish solution was degassed for 15 minutes by bubbling nitrogen through. Copper(I) iodide (1 mg, 5.25 μmol) was added and the mixture heated to 90° C. for 14 h. After cooling to room temperature the reaction mixture was passed through a silica gel pipette and the residue was purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.1% TFA, to give the product as a colorless solid with some TBAF contamination. The residue was purified by column chromatography on silica gel (10 g prepacked) eluting with EtOAc/MeOH to give 3-[4-(2-Methyl-pyridin-4-ylethynyl)-1,2,3-triazol-1-yl]-1-(2,2,2-trifluoro-ethyl)-1,3,4,5-tetrahydro-1-benzazepin-2-one (11 mg) as a colorless solid.

Workup

  1. customthe resulting brownish solution was degassed for 15 minutes
  2. customby bubbling nitrogen through
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. customthe residue was purified by preparative HPLC Reverse phase (C-18)
  5. washeluting with Acetonitrile/Water+0.1% TFA

Sources & evidence

ORD record
ord-30bc5e408d794297a6d6123718b4e882
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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