Triethylamine → HCID 86712481, compound

HRID 630591Notes

Reaction equation

HRID 630591 reaction equation
[CH3:1][C:2]1([CH3:9])[C:6]([CH3:8])([CH3:7])[O:5][BH:4][O:3]1.Br[C:11]1[C:19]2[S:18][CH:17]=[CH:16][C:15]=2[C:14]([F:20])=[CH:13][CH:12]=1.C(N(CC)CC)C>O1CCOCC1.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>[F:20][C:14]1[C:15]2[CH:16]=[CH:17][S:18][C:19]=2[C:11]([B:4]2[O:5][C:6]([CH3:8])([CH3:7])[C:2]([CH3:9])([CH3:1])[O:3]2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 23080028HCID 23080028, compound

Product 1

HCID 86712481HCID 86712481, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

4,4,5,5-Tetramethyl-1,3,2-dioxaborolane (768 mg, 6 mmole) was added drop wise to a solution of 7-bromo-4-fluoro-1-benzothiophene BL (462 mg, 2.0 mmole) and triethylamine (607 mg, 6 mmole) in 12 mL dioxane. The solution was bubbling with argon with stirring for 10 min. PdCl2(PPh3)2 (70 mg, 0.01 mmole) was added to the reaction and continued to bubbling argon for another 10 min. The reaction was heated to 80° C. for 4 hr and cooled down to 25° C. Dioxane was removed in vacuo the residue dissolved in 60 mL Et2O washed with water (60 mL), brine (20 mL), dried (Na2SO4), filtered, concentrated in vacuo, and purified by CombiFlash silica gel column chromatography (eluted with Hexane/EtOAc stepping gradient 100:0 to 80:20) to yield 295 mg (53%) of product.

Workup

  1. customThe solution was bubbling with argon
  2. customto bubbling argon for another 10 min
  3. temperaturecooled down to 25° C
  4. customDioxane was removed in vacuo the residue
  5. dissolutiondissolved in 60 mL Et2O
  6. washwashed with water (60 mL), brine (20 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. custompurified by CombiFlash silica gel column chromatography (eluted with Hexane/EtOAc stepping gradient 100:0 to 80:20)

Sources & evidence

ORD record
ord-8815372568734ba386726f078a641960
Source dataset
uspto-grants-2016_04
Patent number
US09315864B2

Reaction notes

Loading…