Potassium Carbonate → HCID 57855463, compound

HRID 1360648Notes

Reaction equation

HRID 1360648 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([S:12]([CH3:15])(=[O:14])=[O:13])[CH2:9]2)=[CH:4][CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO.O1CCOCC1.CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][N:8]([S:12]([CH3:15])(=[O:14])=[O:13])[CH2:9]3)=[CH:4][CH:3]=2)=[CH:19][CH:18]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 2856454-Fluorophenylboronic acidHCID 57855451HCID 57855451, compound

Product 1

HCID 57855463HCID 57855463, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 7-bromo-2-(methylsulfonyl)-1,2,3,4-tetrahydroisoquinoline (2.90 g, 10.0 mmol), 4-fluorophenylboronic acid (2.10 g, 15.0 mmol), anhydrous potassium carbonate (4.15 g, 30.0 mmol) and triphenylphosphine (525 mg, 2.0 mmol) was prepared in MeOH (20 ml) and 1,4-dioxane (10 ml). Argon was bubbled for 10 min., then Pd(OAc)2 (112 mg, 0.50 mmol) was added. The resulting mixture was refluxed for 5 hours. The reaction mixture was diluted with Et2O (50 ml) and the resulting suspension was filtered trough a pad of Celite. The filtrate was evaporated under reduced pressure. The residue was taken up with Et2O and washed with water (3×) and brine. The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure to give a black oil. After purification by flash chromatography on silica (cHex/EtOAc, gradient from 3/1 to 3/2), the title compound was obtained as a beige solid (2.50 g, 82%). HPLC, Rt: 4.4 min (purity: 98.8%). LC/MS, M+(ESI): 306.2.

Workup

  1. customArgon was bubbled for 10 min.
  2. temperatureThe resulting mixture was refluxed for 5 hours
  3. filtrationthe resulting suspension was filtered trough a pad of Celite
  4. customThe filtrate was evaporated under reduced pressure
  5. washwashed with water (3×) and brine
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customthe solvent was removed under reduced pressure
  8. customto give a black oil
  9. customAfter purification by flash chromatography on silica (cHex/EtOAc, gradient from 3/1 to 3/2)

Sources & evidence

ORD record
ord-56a10d2cf047409781d66d15c9f34f67
Source dataset
uspto-grants-2011_02
Patent number
US07879876B2

Reaction notes

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