3-Butyn-1-OL → RWJ 67657

HRID 1831843Notes

Reaction equation

HRID 1831843 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10](I)[N:11]([CH2:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[CH2:29]([OH:33])[CH2:30][C:31]#[CH:32]>C(NC(C)C)(C)C.[Cu]I>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:32]#[C:31][CH2:30][CH2:29][OH:33])[N:11]([CH2:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 135663-Butyn-1-OLHCID 11059934HCID 11059934, compound

Product 1

HCID 3008319RWJ 67657

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 7912DiisopropylamineSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of 4-(4-fluorophenyl)-2-iodo-1-(3-phenylpropyl)-5-(4-pyridyl)imidazole (1.42 g, 2.74 mmol) and 3-butyn-1-ol (0.289 g, 4.1 mmol) in diisopropylamine (10 mL) was added bis(acetato)-bis(triphenylphosphine) palladium (0.102 g, 0.14 mmol), followed by the addition of copper(I) iodide (0.052 g, 0.274 mmol). The mixture was stirred at 75° C. for 4 h. The reaction mixture was then cooled to room temperature and quenched with water (100 mL). The mixture was extracted with ethyl acetate (2×50 mL). The combined ethyl acetate extract was washed with water (2×30 mL), brine (30 mL), and dried with Na2SO4. After removal of solvents, the crude product was obtained as a brown solid.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customquenched with water (100 mL)
  3. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
  4. extractionThe combined ethyl acetate extract
  5. washwas washed with water (2×30 mL), brine (30 mL)
  6. dry with materialdried with Na2SO4
  7. customAfter removal of solvents

Sources & evidence

ORD record
ord-d1bc8cab252a4fd0ac2cd6ee2f402b52
Source dataset
uspto-grants-2006_06
Patent number
US07067671B2

Reaction notes

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