HCID 10193055, compound → HCID 10236495, compound

HRID 1794523Notes

Reaction equation

HRID 1794523 reaction equation
I[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[OH:13].CN([CH:17]=[O:18])C.N1[CH2:23][CH2:22][CH2:21][CH2:20]1>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>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[C:3]2[O:13][C:21]([C:22]3[CH:23]=[CH:4][C:3]([O:18][CH3:17])=[CH:2][CH:7]=3)=[CH:20][C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 10193055HCID 10193055, compoundHCID 86759967HCID 86759967, compound

Product 1

HCID 10236495HCID 10236495, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

The 2-Iodo-4-methoxy-6-nitro-phenol 97 (1 g, 2.25 mmol based on 0.67 molar purity) in DMF/pyrrolidine (3 mL/3 mL) was treated with 4-methoxystyryne (0.45 g, 3.4 mmol), catalytic PdCl2(PPh3)2 and catalytic Cul was heated at 60° C. until reaction was adjudged complete by TLC analysis (<1 h to completion). The reaction was worked up by partitioning between EtOAc and 2 N HCl aq. The EtOAc was washed with saturated NaHCO3 aq, brine and dried over MgSO4. After filtering and concentrating, the product was purified by trituration with MeOH to give 0.57 g: Mp=141° C.

Workup

  1. customwas adjudged complete by TLC analysis (<1 h to completion)
  2. customby partitioning between EtOAc and 2 N HCl aq. The EtOAc
  3. washwas washed with saturated NaHCO3 aq, brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtering
  6. concentrationconcentrating
  7. customthe product was purified by trituration with MeOH
  8. customto give 0.57 g

Sources & evidence

ORD record
ord-6ebca667a946444893f538e2ed69c328
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

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