Lithium Chloride → HCID 66749418, compound

HRID 537038Notes

Reaction equation

HRID 537038 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11](I)=[N:10][C:9]=1[C:14]([O:16][CH3:17])=[O:15].[CH3:18][C:19]1[C:20]([Sn](C)(C)C)=[CH:21][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[N:23][CH:24]=1.[Cl-].[Li+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[C:26]([NH:25][C:22]1[CH:21]=[C:20]([C:11]2[O:12][C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[C:9]([C:14]([O:16][CH3:17])=[O:15])[N:10]=2)[C:19]([CH3:18])=[CH:24][N:23]=1)(=[O:28])[CH3:27]

Participants

7

Reactant 3

HCID 433294Lithium ChlorideHCID 66747865HCID 66747865, compoundHCID 66749494HCID 66749494, compound

Product 1

HCID 66749418HCID 66749418, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 5-(2-chlorophenyl)-2-iodo-1,3-oxazole-4-carboxylate (3.0 g, 8.3 mmol), N-[5-methyl-4-(trimethylstannyl)pyridine-2-yl]acetamide (2.8 g, 9.1 mmol), tetrakis(triphenylphosphine)palladium(0) (0.48 g, 0.41 mmol), copper(I) iodide (0.47 g, 2.5 mmol) and lithium chloride (1.1 g, 24.8 mmol) in 1,4-dioxane (80 mL) was degassed with argon three times. The mixture was allowed to stir at 100° C. under an atmosphere of argon for 2 h and then filtered while hot. The reaction mixture was concentrated to a small volume and then 10% aqueous ammonia (150 mL) was added. The mixture was filtered and the solid was washed with diethyl ether to give methyl 2-[2-(acetylamino)-5-methylpyridin-4-yl]-5-(2-chlorophenyl)-1,3-oxazole-4-carboxylate (2.3 g, 72%) which was used without further purification.

Workup

  1. customwas degassed with argon three times
  2. filtrationfiltered while hot
  3. concentrationThe reaction mixture was concentrated to a small volume
  4. addition10% aqueous ammonia (150 mL) was added
  5. filtrationThe mixture was filtered
  6. washthe solid was washed with diethyl ether

Sources & evidence

ORD record
ord-7f38d5330e17405b9568fdaaa59cafe3
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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