Propargyl alcohol → HCID 89924003, compound

HRID 1500938Notes

Reaction equation

HRID 1500938 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13](I)[C:5]([NH:6][CH2:7][CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:4]([F:16])[CH:3]=1.[CH2:17]([OH:20])[C:18]#[CH:19]>CCN(CC)CC.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[CH:14]=[C:13]2[C:5](=[C:4]([F:16])[CH:3]=1)[N:6]([CH2:7][CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:18]([CH2:17][OH:20])=[CH:19]2

Participants

6

Reactant 2

HCID 7859Propargyl alcoholHCID 899240084-chloro-2-fluoro-6-iodo-N-(2-(methylsulfonyl)ethyl)aniline

Product 1

HCID 89924003HCID 89924003, compoundYield 95.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 4-chloro-2-fluoro-6-iodo-N-(2-(methylsulfonyl)ethyl)aniline (450 mg, 1.2 mmol) and prop-2-yn-1-ol (135 mg, 2.4 mmol) in Et3N (20 ml) was degassed and refluxed under N2 atmosphere. PdCl2(PPh3)2 (90 mg, 0.12 mmol) and CuI (45 mg, 0.24 mmol) were added successively to the reaction mixture. After being stirred under reflux overnight, the mixture was concentrated in vacuo and the residue was poured into water and extracted with EtOAc (50 mL×3). The combined organic layers were dried over Na2SO4 and then concentrated in vacuo. The residue was purified by preparative-TLC (PE: EtOAc=5:1) to give {5-chloro-7-fluoro-1-[2-(methylsulfonyl)ethyl]-1H-indol-2-yl}methanol as a yellow solid (350 mg, yield: 95%).

Workup

  1. customwas degassed
  2. temperaturerefluxed under N2 atmosphere
  3. temperatureunder reflux overnight
  4. concentrationthe mixture was concentrated in vacuo
  5. additionthe residue was poured into water
  6. extractionextracted with EtOAc (50 mL×3)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by preparative-TLC (PE: EtOAc=5:1)

Sources & evidence

ORD record
ord-1b7f992032a34b73941a164c3a4a477a
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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