Tetrahydrofuran → HCID 67517345, compound

HRID 2173138Notes

Reaction equation

HRID 2173138 reaction equation
[Br:1][C:2]1[C:3](I)=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][CH2:6][CH2:5]2.F[C:15](OB([O-])[O-])(F)F.[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].C1COCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.O>[Br:1][C:2]1[C:3]([CH3:15])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][CH2:6][CH2:5]2

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 67517319HCID 67517319, compoundHCID 131732965HCID 131732965, compound

Product 1

HCID 67517345HCID 67517345, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

To a 20 mL microwave tube was added 6-Bromo-5-iodo-3,4-dihydro-1H-isochromen-1-one (300 mg, 0.85 mmol), Potassium Trifluoromethylborate (114 mg, 0.94 mmol), PdCl2(dppf)-CH2Cl2 Adduct (69 mg, 0.085 mmol), cesium carbonate (830 mg, 2.6 mmol), and a stir bar. The mixture was sealed and THF (10 mL) and water (1 mL) were added with a syringe. The mixture was purged three times with nitrogen, and then heated to 140° C. for 30 minutes. TLC showed formation of the desired product. The reaction was diluted with EtOAc, washed with water and brine, dried over sodium sulfate, adsorbed onto silica gel, and purified by MPLC (Hex/EtOAc gradient) to furnish the product. LC-MS (IE, m/z): 241 [M+1]+;

Workup

  1. customThe mixture was sealed
  2. customThe mixture was purged three times with nitrogen
  3. additionThe reaction was diluted with EtOAc
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. custompurified by MPLC (Hex/EtOAc gradient)
  7. customto furnish the product

Sources & evidence

ORD record
ord-03441c177f8e48ed9c4e7a81c3c141d9
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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