Triethylamine → HCID 86673012, compound

HRID 1851659Notes

Reaction equation

HRID 1851659 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)#[CH:10].C(N(CC)CC)C>C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:10]#[C:9][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 5226271-Ethynyl-4-fluorobenzeneHCID 17142232-Chloro-5-iodopyrimidine

Product 1

HCID 86673012HCID 86673012, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-chloro-5-iodopyrimidine (600 mg, 2.5 mmol), 1-ethynyl-4-fluorobenzene (330 mg, 2.75 mmol), triethylamine (556 mg, 761 μl, 5.49 mmol), and bis(triphenyl-phosphine)palladium (II) chloride (175 mg, 250 μmol) in 7 ml of THF was purged with argon. Then copper (I) iodide (23.8 mg, 125 μmol) was added and the reaction was heated for 2 h at room temperature. The dark solution was filtered and the solids were washed with THF. The residue was taken up in ethyl acetate, adsorbed onto 3 g of silicagel which was loaded onto a 50 g prepacked flash chromatography column. After elution with a 0% to 20% ethyl acetate in heptane gradient, the fractions containing the desired product were collected to yield 505 mg (87%) of the title compound as an crystalline light yellow solid, MS: m/e=233.1, 235.1 (M+H+).

Workup

  1. filtrationThe dark solution was filtered
  2. washthe solids were washed with THF
  3. washAfter elution with a 0% to 20% ethyl acetate in heptane gradient
  4. additionthe fractions containing the desired product
  5. customwere collected

Sources & evidence

ORD record
ord-6f2b3ab36de34c09bbf0942f96103144
Source dataset
uspto-grants-2015_02
Patent number
US08957213B2

Reaction notes

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