Tributylphenyltin → HCID 178472765, compound

HRID 1423951Notes

Reaction equation

HRID 1423951 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][NH:6][C:7]([C:9]1[C:10](=[O:22])[S:11][C:12]2[C:17]([C:18]=1[OH:19])=[CH:16][C:15]([Cl:20])=[CH:14][C:13]=2Br)=[O:8])[CH3:2].C([Sn](CCCC)(CCCC)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)CCC>CN(C=O)C.C(OCC)(=O)C.O.C1(P([Pd-2](Cl)(Cl)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][NH:6][C:7]([C:9]1[C:10](=[O:22])[S:11][C:12]2[C:17]([C:18]=1[OH:19])=[CH:16][C:15]([Cl:20])=[CH:14][C:13]=2[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:8])[CH3:2]

Participants

7

Reactant 2

HCID 607632TributylphenyltinHCID 178472764HCID 178472764, compound

Product 1

HCID 178472765HCID 178472765, compoundYield 83.4%

Reagents, catalysts & solvents 4

HCID 178418903HCID 178418903, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

[(8-Bromo-6-chloro-4-hydroxy-2-oxo-2H-thiochromene-3-carbonyl)-amino]-acetic acid ethyl ester (22(d)) (500 mg, 1.2 mmol) was dissolved in anhydrous DMF (5 mL). To the solution was added Tributyl-phenyl-stannane (467 uL, 1.43 mmol), bis(triphenylphosphino) palladium(II) dichloride (100 mg, 0.12 mmol) and 4 A molecular sieves. The reaction was sealed and the solution was heated to 120 C for 45 minutes. The reaction was cooled, diluted with ethyl acetate (25 mL) and water (25 mL). The organic phase was separated, dried over magnesium sulfate and concentrated residue in vacuo. The residue was filtered through silica to provide the title compound (418 mg) which was used directly without further purification.

Workup

  1. customThe reaction was sealed
  2. temperaturethe solution was heated to 120 C for 45 minutes
  3. temperatureThe reaction was cooled
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulfate and concentrated residue in vacuo
  6. filtrationThe residue was filtered through silica

Sources & evidence

ORD record
ord-70a8c1ae4b904104b5580738f3f86503
Source dataset
uspto-grants-2015_01
Patent number
US08927591B2

Reaction notes

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