Potassium Phosphate, Tribasic → HCID 20318602, compound

HRID 1793248Notes

Reaction equation

HRID 1793248 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(C1C=C(NS(C)(=O)=O)C(OC)=C(NC([C:22]2[N:23](C)[C:24]3[C:29]([CH:30]=2)=[CH:28][CH:27]=[CH:26][C:25]=3[O:31][C:32]2C=CN=C(C(=O)NC)[CH:33]=2)=O)C=1)(C)(C)C>CC([O-])=O.CC([O-])=O.[Pd+2]>[NH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:30]=[CH:22]1.[CH3:24][CH2:25][O:31][CH2:32][CH3:33]

Participants

4

Reactant 2

HCID 62657Potassium Phosphate, TribasicHCID 11949922HCID 11949922, compound

Product 1

HCID 20318602HCID 20318602, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
100 °C

Procedure

A Schlenk tube was charged with Pd(OAc)2 (16 mg, 0.07 mmol), K3PO4 (525 mg, 2.40 mmol), di-t-butylbiphenylphosphine (42 mg, 0.14 mmol) and the 7-hydroxyindole ester (see Example 6) (307 mg, 1.4 mmol), and capped with a septum and purged with argon. A solution of the benzyl ether from above (270 mg, 1.16 mmol) in 3 mL of toluene was then added via syringe. The mixture was heated at 100° C. with stirring under argon for 6 h. The reaction mixture was filtered through a layer of diatomaceous earth and the solid residue was rinsed with CH2Cl2. The combined filtrate was concentrated. The crude product was purified by column chromatography to give 61% yield of the desire indole ether.

Workup

  1. custompurged with argon
  2. additionA solution of the benzyl ether from above (270 mg, 1.16 mmol) in 3 mL of toluene was then added via syringe
  3. filtrationThe reaction mixture was filtered through a layer of diatomaceous earth
  4. washthe solid residue was rinsed with CH2Cl2
  5. concentrationThe combined filtrate was concentrated
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-d793debe87e84fa9bb83bfe2b15e1506
Source dataset
uspto-grants-2006_07
Patent number
US07078419B2

Reaction notes

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