Tetrahydrofuran → HCID 58072081, compound

HRID 715688Notes

Reaction equation

HRID 715688 reaction equation
O1CCC[CH2:2]1.Br[C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:17][CH3:18])[C:14]=1[O:15][CH3:16])[C:10]#[N:11].CB1OB(C)OB(C)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>O.C(OCC)(=O)C.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]>[CH3:18][O:17][C:13]1[CH:12]=[C:9]([CH:8]=[C:7]([CH3:2])[C:14]=1[O:15][CH3:16])[C:10]#[N:11]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 574072TrimethylboroxineHCID 7355263-bromo-4,5-dimethoxybenzonitrile

Product 1

HCID 58072081HCID 58072081, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

50 mg [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium (II) and 5 mL tetrahydrofuran was stirred for 10 min at ambient temperature before 500 mg 3-bromo-4,5 dimethoxybenzonitrile, 0.1 mL trimethylboroxine and 0.85 g cesium carbonate as a solution in 1 mL water were added. The suspension was stirred at 100° C. for 4 h and then diluted with water and ethyl acetate. The phases were separated and the water phase was extracted with additional ethyl acetate (×2). The organic phases were combined, dried over magnesium sulfate and concentrated. The residue was purified with silica gel chromatography (SiO2: cyclohexane/ethyl acetate 9:1 to 7:3) to provide 4.17.

Workup

  1. additionwere added
  2. customThe phases were separated
  3. extractionthe water phase was extracted with additional ethyl acetate (×2)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel chromatography (SiO2: cyclohexane/ethyl acetate 9:1 to 7:3)
  7. customto provide 4.17

Sources & evidence

ORD record
ord-c6b948298d8b44798073e53c993e1417
Source dataset
uspto-grants-2015_11
Patent number
US09187478B2

Reaction notes

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