Triethylamine → HCID 59511407, compound

HRID 1159881Notes

Reaction equation

HRID 1159881 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[C:16]([C:18]1[CH:19]=[C:20]([NH:24][C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])[CH:21]=[CH:22][CH:23]=1)#[CH:17]>C1COCC1.C(Cl)Cl.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.[Cu]I>[Cl:1][C:2]1[N:7]=[C:6]([C:17]#[C:16][C:18]2[CH:19]=[C:20]([NH:24][C:25](=[O:30])[C:26]([F:27])([F:28])[F:29])[CH:21]=[CH:22][CH:23]=2)[CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 59513885N-(3-ethynylphenyl)-2,2,2-trifluoroacetamide

Product 1

HCID 59511407HCID 59511407, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a mixture of 2,4-dichloropyrimidine (14.5 g, 97.5 mmol), dichlorobis(triphenyl-phosphine)palladium(II) (1.3 g, 2.6 mmol), and copper(I) iodide (25 mg, 0.13 mmol) in degassed THF was added triethylamine (34 mL, 263 mmol), and the mixture was heated to 50° C. A solution of N-(3-ethynyl-phenyl)-2,2,2-trifluoro-acetamide (14 g, 65 mmol) in THF was added to the mixture over 45 min. After several h, the reaction was cooled to rt and diluted with DCM. The organic mixture was washed with water and brine, dried over MgSO4 and concentrated. The crude material was purified through silica to give the title compound as an off-white solid. 1H NMR (400 MHz, d6-DMSO): δ 11.43 (s, 1H), 8.83 (d, J=4.8 Hz, 1H), 8.00 (s, 1H), 7.80 (d, J=4.8 Hz, 1H), 7.76 (m, 1H), 7.54-7.52 (m, 2H).

Workup

  1. temperatureAfter several h, the reaction was cooled to rt
  2. washThe organic mixture was washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude material was purified through silica

Sources & evidence

ORD record
ord-4f55b58675bc42048c8b4067f26a636c
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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