Lithium Chloride → HCID 54473510, compound

HRID 433864Notes

Reaction equation

HRID 433864 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([Sn](C)(C)C)=[CH:16][CH:15]=2)[N:13]=1.[C:24]([CH2:27][CH2:28][NH:29][C:30]1[CH:35]=[CH:34][C:33](I)=[CH:32][N:31]=1)(=[O:26])[CH3:25].[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>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([C:33]3[CH:34]=[CH:35][C:30]([NH:29][CH2:28][CH2:27][C:24](=[O:26])[CH3:25])=[N:31][CH:32]=3)=[CH:16][CH:15]=2)[N:13]=1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 18755942HCID 18755942, compoundHCID 53847333HCID 53847333, compound

Product 1

HCID 54473510HCID 54473510, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

2-(2,6-Difluorophenyl)-4-(4-trimethylstannylphenyl)oxazoline (0.84 g, 2.0 mmol) was mixed with 2-(N-acetylethylamino)-5-iodopyridine (0.93 g, 3.2 mmol), Pd(PPh3)4 (0.12 g) and lithium chloride (0.15 g) in dioxane (10 ml) and the mixture was refluxed for 8 hours. After separation by chromatography (eluent: ethyl acetate), 2-(2,6-difluorophenyl)-4-[4-(2-(N-acetylethylamino)pyridin-5-yl)phenyl]oxazoline was obtained, 0.31 g, pale oil.

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. customAfter separation by chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-93d8cb272f7a481595912d4e215e1cf8
Source dataset
uspto-grants-2003_12
Patent number
US06670307B2

Reaction notes

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