Triethylamine → HCID 19423432, compound

HRID 1464186Notes

Reaction equation

HRID 1464186 reaction equation
[F:1][C:2]1[C:12](I)=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([OH:14])[CH:3]=1.[C:15]([C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:26][C:27]2[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][N:28]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=1)#[CH:16].C(N(CC)CC)C>O1CCCC1.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>[F:1][C:2]1[C:12]([C:16]#[C:15][C:17]2[CH:18]=[CH:19][C:20]([S:23]([NH:26][C:27]3[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][N:28]=3)(=[O:24])=[O:25])=[CH:21][CH:22]=2)=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([OH:14])[CH:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 19423390HCID 19423390, compoundHCID 194234204-ethynyl-N-(3-methyl-2-pyridinyl)benzenesulfonamide

Product 1

HCID 19423432HCID 19423432, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 4-fluoro-2-hydroxy-5-iodobenzoate (3.6 g, 80%, 10 mmol), 4-ethynyl-N-(3-methyl-2-pyridinyl)benzenesulfonamide (2.7 g, 10 mmol) and triethylamine (5 g, 50 mmol) were suspended in tetrahydrofuran (20 ml) and the mixture heated to 50° C. Dichlorobis(triphenylphosphine)palladium (45 mg, 0.06 mmol) and copper(I)iodide (76 mg, 0.4 mmol) were added with stirring. After about 15 min a practically clear solution had formed. After 3 h at 50° C. the solution was taken to dryness and triturated with isobutylmethylketone and dilute hydrochloric acid. The organic phase was separated and the solvent evaporated. The oily residue was triturated with a small amount of acetonitrile to form crystals. These were recrystallized from acetic acid. The product was dissolved in a small amount of chloroform and the solution applied on top of a short silica gel column and eluted with 25% isobutylmethylketone in toluene. The pure product resulted after evaporation of the solvent Yield 2.0 g, 44%.

Workup

  1. customAfter about 15 min a practically clear solution had formed
  2. customtriturated with isobutylmethylketone and dilute hydrochloric acid
  3. customThe organic phase was separated
  4. customthe solvent evaporated
  5. customThe oily residue was triturated with a small amount of acetonitrile
  6. customto form crystals
  7. customThese were recrystallized from acetic acid
  8. dissolutionThe product was dissolved in a small amount of chloroform
  9. washeluted with 25% isobutylmethylketone in toluene
  10. customThe pure product resulted
  11. customafter evaporation of the solvent Yield 2.0 g, 44%

Sources & evidence

ORD record
ord-c9f9afc13ec14619a05243ea239c63d6
Source dataset
uspto-grants-1994_04
Patent number
US05302718

Reaction notes

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