Triethylamine → HCID 21040466, compound

HRID 705473Notes

Reaction equation

HRID 705473 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[C:10]1([CH:16]=[CH:17][CH:18]([OH:21])[C:19]#[CH:20])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu](I)I>[O:21]=[C:18](/[CH:17]=[CH:16]/[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)/[CH:19]=[CH:20]/[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 12162Benzonitrile, 4-bromo-HCID 570771HCID 570771, compound

Product 1

HCID 21040466HCID 21040466, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

4-bromobenzonitrile (182 mg, 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 ethyl acetate (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, 30% ethyl acetate in dichloromethane). This gave pure final compound TG007A82 (160 mg, 62%) as a light yellow powder.

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 ethyl acetate (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, 30% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-936e557a2f534ae1ae09c71a4f354576
Source dataset
uspto-grants-2015_11
Patent number
US09174960B2

Reaction notes

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