Water → HCID 57471437, compound

HRID 2177117Notes

Reaction equation

HRID 2177117 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[CH2:13][CH2:12][CH:11]([NH:17][C:18](OCC)=[O:19])[CH:10]([CH2:23][C:24]3[CH:29]=[CH:28][C:27](Cl)=[C:26](Cl)[CH:25]=3)[C:9]=2[CH:8]=1)(=O)=O.[CH2:34]([NH:37][S:38]([CH2:41][CH2:42][CH3:43])(=[O:40])=[O:39])[C:35]#[CH:36].[CH2:44](N(CC)CC)C.O>O1CCOCC1.[Cu]I>[CH2:23]([CH:10]1[C:9]2[C:14](=[CH:15][CH:16]=[C:7]([C:36]#[C:35][CH2:34][NH:37][S:38]([CH2:41][CH2:42][CH3:43])(=[O:40])=[O:39])[CH:8]=2)[CH2:13][CH2:12][CH:11]1[NH:17][C:18](=[O:19])[CH3:44])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 46870536HCID 46870536, compoundHCID 61342476HCID 61342476, compound

Product 1

HCID 57471437HCID 57471437, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

7-Acetamido-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (100 mg, 0.234 mmol; prepared in analogy to 8-(3,4-dichlorobenzyl)-7-[(ethoxycarbonyl)amino]-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate, example 29), N-(prop-2-ynyl)propane-1-sulfonamide (75 mg, 0.468 mmol), palladium tetrakistriphenylphosphine (54 mg, 0.047 mmol), copper(I) iodide (35.6 mg, 0.187 mmol) and triethylamine (65 μL, 0.468 mmol) in dioxane (3 mL) were heated under reflux for 16 h. Water (15 mL) was added and the mixture extracted with dichloromethane (3×20 mL). The combined organic extracts were dried (MgSO4) and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography (silica gel, dichloromethane, methanol). Yield: 56 mg (0.132 mmol, 57%).

Workup

  1. temperatureunder reflux for 16 h
  2. extractionthe mixture extracted with dichloromethane (3×20 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. customthe solvent was evaporated in vacuo
  5. customThe crude product was purified by flash chromatography (silica gel, dichloromethane, methanol)

Sources & evidence

ORD record
ord-5c377def7a524575aafa85955c4b7447
Source dataset
uspto-grants-2015_06
Patent number
US09067871B2

Reaction notes

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