Triethylamine → 2-(6-chloro-5-fluoro-1-methanesulfonyl-1H-indol-2-yl)-1-ethylsulfanyl-propan-2-ol

HRID 1945162Notes

Reaction equation

HRID 1945162 reaction equation
[Cl:1][C:2]1[C:3]([F:14])=[CH:4][C:5](I)=[C:6]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:7]=1.C(N(CC)CC)C.[CH2:22]([S:24][CH2:25][C:26]([CH3:30])([OH:29])[C:27]#[CH:28])[CH3:23]>O1CCCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5]([CH:28]=[C:27]([C:26]([OH:29])([CH3:30])[CH2:25][S:24][CH2:22][CH3:23])[N:8]2[S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[F:14]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 589795961-Ethylsulfanyl-2-methyl-but-3-yn-2-olHCID 66865370N-(5-chloro-4-fluoro-2-iodo-phenyl)-methanesulfonamide

Product 1

HCID 115886722-(6-chloro-5-fluoro-1-methanesulfonyl-1H-indol-2-yl)-1-ethylsulfanyl-propan-2-ol

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a 50 mL round-bottom flask were added N-(5-chloro-4-fluoro-2-iodo-phenyl)-methanesulfonamide (0.30 g, 1.0 mmol), bis(triphenylphosphine) palladium(II) chloride (35 mg, 0.05 mmol) and copper (I) iodide (19 mg, 0.1 mmol). The flask was fitted with a septum and stirred under argon. Tetrahydrofuran (5 mL) and triethylamine (0.28 mL, 2.0 mmol) were then added via syringe. 1-Ethylsulfanyl-2-methyl-but-3-yn-2-ol (0.14 g, 1.0 mmol) in tetrahydrofuran (1 mL) was added via syringe and the reaction maintained with stirring at 50-60° C. for four hours. The solution was evaporated and the residue purified by column chromatography using dichloromethane as solvent to yield the title compound as a brown oil.

Workup

  1. customThe flask was fitted with a septum
  2. temperaturethe reaction maintained
  3. stirringwith stirring at 50-60° C. for four hours
  4. customThe solution was evaporated
  5. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-2b31213b7be2482688a5422152cd0e4d
Source dataset
uspto-grants-2013_03
Patent number
US08394971B2

Reaction notes

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