Sodium Fluoride → HCID 22280642, compound

HRID 354029Notes

Reaction equation

HRID 354029 reaction equation
[C:1]([NH:8][C:9]1[S:10][C:11](Br)=[C:12]([C:14]([O:16][CH2:17][P:18]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:19])=[O:15])[N:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:27]([Sn](CCCC)(CCCC)C=C)[CH2:28]CC.[F-].[Na+]>CN(C=O)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>[C:1]([NH:8][C:9]1[S:10][C:11]([CH:27]=[CH2:28])=[C:12]([C:14]([O:16][CH2:17][P:18]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:19])=[O:15])[N:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

7

Reactant 3

HCID 5235Sodium FluorideHCID 81998TributylvinyltinHCID 22280687HCID 22280687, compound

Product 1

HCID 22280642HCID 22280642, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-[N-Boc(amino)]-5-bromo-4-diethylphosphonomethoxycarbonylthiazole (1 mmole) and dichlorobis(triphenylphosphine)palladium(II) (0.1 mmole) in DMF (5 mL) was treated with tributyl(vinyl)tin (2.5 mmole) and the reaction was stirred at 60° C. for 2 h. The solvent was removed and the residue taken up in EtOAc and stirred with 2 mmol NaF in 5 ml water for 1 h. Extraction and chromatography gave 2-[N-Boc(amino)]-5-vinyl-4-diethylphosphonomethoxycarbonylthiazole as a yellow solid.

Workup

  1. customThe solvent was removed
  2. extractionExtraction and chromatography

Sources & evidence

ORD record
ord-5449a52d1ba140e0a22764edffeaccbf
Source dataset
uspto-grants-2004_06
Patent number
US06756360B1

Reaction notes

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