Triethylamine → HCID 18446620, compound

HRID 1269079Notes

Reaction equation

HRID 1269079 reaction equation
[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][N:3]=1.[CH3:9][CH:10]([OH:13])[C:11]#[CH:12].C(N(CC)CC)C>[Cu]I.CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([C:12]#[C:11][CH:10]([OH:13])[CH3:9])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 162393-Butyn-2-olHCID 70235702-Fluoro-4-iodopyridine

Product 1

HCID 18446620HCID 18446620, compoundYield 66%

Reagents, catalysts & solvents 2

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

Procedure

A solution of 2-fluoro-4-iodopyridine (3.0 g, 13 mmol), 3-butyn-2-ol (2.1 mL, 26 mmol), dichlorobis(triphenylphosphine) palladium (II) (0.9 g, 1.3 mmol), copper (I) iodide (0.5 g, 2.6 mmol), triethylamine (5.4 mL 39 mmol), and anhydrous N,N-dimethylformamide (20 mL) were heated to 75° C. for 4 hours. When judged to be complete, the mixture was partitioned between ethyl acetate and water, the organics were washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude mixture was purified using flash chromatography (4:1 hexanes:ethyl acetate) to provide 4-(2-fluoro-4-pyridinyl)-3-butyn-2-ol (1.4 g, 66%) as an orange oil. 1H NMR (DMSO-d6): δ 8.21 (d, 1H), 7.32 (d, 1H), 7.20 (s, 1H), 5.62 (d, 1H), 4.61 (m, 1H), 1.36 (d, 3H).

Workup

  1. customthe mixture was partitioned between ethyl acetate and water
  2. washthe organics were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude mixture was purified

Sources & evidence

ORD record
ord-df3338b202da4278aedcf9220c046132
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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