Tributylphenyltin → HCID 68428570, compound

HRID 642421Notes

Reaction equation

HRID 642421 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](Br)[C:9]2[N:10]([CH3:20])[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([Sn](CCCC)(CCCC)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)CCC>CN(C=O)C.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]([CH3:20])[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

5

Reactant 2

HCID 607632TributylphenyltinHCID 86617365HCID 86617365, compound

Product 1

HCID 68428570HCID 68428570, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-bromo-4-hydroxy-9-methyl-9H-beta-carboline-3-carboxylic acid ethyl ester (150 mg), tributyl phenyl tin (0.169 mL), and Pd(PPh3)2Cl2 (15 mg) in DMF (1.5 mL) was heated at 120° C. for 41 min. The reaction was then partitioned between EtOAc and water, the organic phase was subsequently washed with sat. NaCl solution, dried over anhydrous sodium sulfate and then filtered, concentrated; the residue was purified with column to give the title compound (94 mg). ESI MS (m/z): 347 (M+H)+.

Workup

  1. customThe reaction was then partitioned between EtOAc and water
  2. washthe organic phase was subsequently washed with sat. NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified with column

Sources & evidence

ORD record
ord-855dce54d6bd403480f58f52c90ec5db
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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