2-Amino-5-methylthiazole → HCID 86683953, compound

HRID 407669Notes

Reaction equation

HRID 407669 reaction equation
[CH3:1][C:2]1[S:6][C:5]([NH2:7])=[N:4][CH:3]=1.Br[C:9]1[C:10](=[O:17])[N:11]([CH3:16])[CH:12]=[C:13]([Br:15])[CH:14]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Br:15][C:13]1[CH:14]=[C:9]([NH:7][C:5]2[S:6][C:2]([CH3:1])=[CH:3][N:4]=2)[C:10](=[O:17])[N:11]([CH3:16])[CH:12]=1

Participants

6

Reactant 3

HCID 3517702-Amino-5-methylthiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-one

Product 1

HCID 86683953HCID 86683953, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 1,4-dioxane (50 mL), 5-methylthiazol-2-amine (2.28 g, 20.0 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (5.34 g, 20.0 mmol) cesium carbonate (13.0 g, 40.0 mmol), xantphos (1.16 g, 2.0 mmol), and tris(dibenzylideneacetone)dipalladium(0) (916 mg, 1.0 mmol). The system was subjected to three cycles of vacuum/argon flush and heated at reflux for 5 h. It was then cooled to room temperature and filtered. The solid was washed with dichloromethane (3×50 mL). The combined filtrate was concentrated under reduced pressure and the residue was washed with acetonitrile (30 mL) to afford 120a (5 g, crude, 83%) as a yellow solid. MS-ESI: [M+H]+ 300.1.

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. customflush
  3. temperatureheated
  4. temperatureat reflux for 5 h
  5. filtrationfiltered
  6. washThe solid was washed with dichloromethane (3×50 mL)
  7. concentrationThe combined filtrate was concentrated under reduced pressure
  8. washthe residue was washed with acetonitrile (30 mL)

Sources & evidence

ORD record
ord-79e45725c1d840eaa4f2ee16a3fffad5
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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