Tetramethyltin → HCID 68428278, compound

HRID 642420Notes

Reaction equation

HRID 642420 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].[CH3:22][Sn](C)(C)C>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]([CH3:22])[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 11661TetramethyltinHCID 86617365HCID 86617365, compound

Product 1

HCID 68428278HCID 68428278, 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 (197 mg), tetramethyl tin (0.094 mL), and Pd(PPh3)2Cl2 (20 mg) in DMF (2 mL) was heated at 120° C. for 45 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 (118 mg). ESI MS (m/z): 285 (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-4c7a42ed16d24e1bbe77b05296e861e5
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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