Tributylphenyltin → HCID 68426574, compound

HRID 642265Notes

Reaction equation

HRID 642265 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](Br)[C:9]2[N:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:11]3[C:16]([C:17]=2[C:18]=1[OH:19])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].[C:27]1([Sn](CCCC)(CCCC)CCCC)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C.CCOC(C)=O.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>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:9]2[N:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:11]3[C:16]([C:17]=2[C:18]=1[OH:19])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 607632TributylphenyltinHCID 86617352HCID 86617352, compound

Product 1

HCID 68426574HCID 68426574, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 1-bromo-4-hydroxy-9-phenyl-9H-beta-carboline-3-carboxylic acid ethyl ester (91 mg, 0.221 mmol), phenyltributyltin (98 mg, 0.265 mmol), and Pd(PPh3)2Cl2 (8 mg, 0.011 mmol) in DMF (1 mL) was stirred at 130° C. for 40 min. The mixture was then diluted with EtOAc, washed with water and saturated NaCl aqueous solution, respectively; the EtOAc phase was dried over anhydrous sodium sulfate, concentrated, and the residue was purified by column to give a white solid, the desired title compound. The title compound, ESI MS (m/z): 409 (M+H+).

Workup

  1. washwashed with water and saturated NaCl aqueous solution
  2. dry with materialthe EtOAc phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customthe residue was purified by column
  5. customto give a white solid

Sources & evidence

ORD record
ord-e15ebe8f78fe45da84f718345c31a22d
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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