Triethylamine → HCID 68181951, compound

HRID 705474Notes

Reaction equation

HRID 705474 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[C:12]1([CH:18]=[CH:19][CH:20]([OH:23])[C:21]#[CH:22])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>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)I>[C:12]1(/[CH:18]=[CH:19]/[C:20](=[O:23])/[CH:21]=[CH:22]/[C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 570771HCID 570771, compound

Product 1

HCID 68181951HCID 68181951, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

4-iodobenzotrifluoride (150 μL, 1 mmol), phenylpent-1-en-4-yn-3-ol (190 mg, 1.2 mmol), bis(triphenylphosphine)palladium(II) dichloride (14 mg, 0.02 mmol), copper iodide (3 mg, 0.03 mmol) and triphenylphosphine (52 mg, 0.2 mmol) were introduced in a 10 mL microwave vial flushed with argon. This was diluted with anhydrous triethylamine (700 μL, 4 mmol) in anhydrous degased 1,4-dioxane (1.3 mL). The solution was heated under microwave irradiation at 120° C. for 45 min. The reaction mixture was poured into a mix of 1M aqueous solution of hydrochloric acid (10 mL) and saturated aqueous ammonium chloride solution (10 mL), and this was extracted with dichloromethane (3×15 mL). The combined organic layers were dried over magnesium sulfate, filtered, and evaporated to dryness to give crude product which was purified by flash chromatography (SiO2, DCM/Hexanes 3:7). The resulting yellow solid was recrystallized (EtOH/Hexanes 1:3) to give pure final compound TG008A86 as a pale yellow powder (155 mg, 51%).

Workup

  1. customvial flushed with argon
  2. customin anhydrous degased 1,4-dioxane (1.3 mL)
  3. additionThe reaction mixture was poured into
  4. additiona mix of 1M aqueous solution of hydrochloric acid (10 mL) and saturated aqueous ammonium chloride solution (10 mL)
  5. extractionthis was extracted with dichloromethane (3×15 mL)
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customto give crude product which
  10. customwas purified by flash chromatography (SiO2, DCM/Hexanes 3:7)
  11. customThe resulting yellow solid was recrystallized (EtOH/Hexanes 1:3)

Sources & evidence

ORD record
ord-57d12df533a044c9968b192e1352b127
Source dataset
uspto-grants-2015_11
Patent number
US09174960B2

Reaction notes

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