Triethylamine → HCID 52936702, compound

HRID 705475Notes

Reaction equation

HRID 705475 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.[CH3:12][N:13]([CH3:26])[C:14]1[CH:19]=[CH:18][C:17]([CH:20]=[CH:21][CH:22]([OH:25])[C:23]#[CH:24])=[CH:16][CH:15]=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>[CH3:26][N:13]([CH3:12])[C:14]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22](=[O:25])/[CH:23]=[CH:24]/[C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 123616390HCID 123616390, compound

Product 1

HCID 52936702HCID 52936702, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

4-iodobenzotrifluoride (150 μL, 1 mmol), 1-(4-(dimethylamino)phenyl)pent-1-en-4-yn-3-ol (242 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 brine (20 mL), and this was extracted with dichloromethane (3×20 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, 30% ethyl acetate in dichloromethane). The resulting yellow solid was triturated in diethyl ether to give pure final compound TG009A94 as a bright orange powder (200 mg, 58%).

Workup

  1. customvial flushed with argon
  2. customin anhydrous degased 1,4-dioxane (1.3 mL)
  3. additionThe reaction mixture was poured into brine (20 mL)
  4. extractionthis was extracted with dichloromethane (3×20 mL)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customto give crude product which
  9. customwas purified by flash chromatography (SiO2, 30% ethyl acetate in dichloromethane)
  10. customThe resulting yellow solid was triturated in diethyl ether

Sources & evidence

ORD record
ord-e1aa17dc37d843d88bc3ae7eed18d848
Source dataset
uspto-grants-2015_11
Patent number
US09174960B2

Reaction notes

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