Lithium Chloride → HCID 11731669, compound

HRID 1385870Notes

Reaction equation

HRID 1385870 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](Br)=[CH:16][CH:15]=2)[N:13]=1.[CH2:21]([O:23][C:24]1[CH:29]=[CH:28][C:27]([Sn](C)(C)C)=[CH:26][N:25]=1)[CH3:22].[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:27]3[CH:28]=[CH:29][C:24]([O:23][CH2:21][CH3:22])=[N:25][CH:26]=3)=[CH:16][CH:15]=2)[N:13]=1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 11046011HCID 11046011, compoundHCID 11119677HCID 11119677, compound

Product 1

HCID 11731669HCID 11731669, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

2-(2,6-Difluorophenyl)4-(4-bromophenyl)oxazoline (VP4) (5.00 g, 14.8 mmol) was mixed with 2-ethoxy-5-trimethylstannylpyridine (VP8) (5.06 g, 17.8 mmol), Pd(PPh3)4 (0.68 g, 0.59 mmol) and lithium chloride (0.12 g, 2.9 mmol) in dioxane (40 ml) and the mixture was refluxed under nitrogen (7 hours). After extraction and chromatography, 2-(2,6-difluorophenyl)4-[4-(2-ethoxypyridin-5-yl)phenyl]oxazoline was obtained, 3.86 g, m.p. 119° C.; 1H NMR (CDCl3, ppm): 1.42, 4.35, OCH2CH3; 4.40, 4.84, 5.51, oxazoline; 6.79, 7.77, 8.36, pyridine; 7.00, 7.41, 7.54, phenyl.

Workup

  1. temperaturethe mixture was refluxed under nitrogen (7 hours)
  2. extractionAfter extraction and chromatography

Sources & evidence

ORD record
ord-a03710259fbf4cb09a121b4927ef9d9d
Source dataset
uspto-grants-2001_07
Patent number
US06265350B1

Reaction notes

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