Lithium Chloride → HCID 18755925, compound

HRID 1385872Notes

Reaction equation

HRID 1385872 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:24][C:25]1[CH:30]=[CH:29][C:28]([Sn](C)(C)C)=[CH:27][N:26]=1)[CH2:22][CH3:23].[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:28]3[CH:29]=[CH:30][C:25]([O:24][CH2:21][CH2:22][CH3:23])=[N:26][CH:27]=3)=[CH:16][CH:15]=2)[N:13]=1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 11046011HCID 11046011, compoundHCID 18755944HCID 18755944, compound

Product 1

HCID 18755925HCID 18755925, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

2-(2,6-Difluorophenyl)4-(4-bromophenyl)oxazoline (VP4) (2.0 g, 2.9 mmol) was mixed with 2-n-propyloxy-5-trimethylstannylpyridine (4.6 g, 50%, 7.7 mmol), Pd(PPh3)4 (0.35 g, 0.3 mmol) and lithium chloride (50 mg) in dioxane and refluxed under nitrogen (7 hours). After chromatography and recrystallization in heptane/ethyl acetate 95:5, 2-(2,6-difluorophenyl)4-[4-(2-n-propyloxypyridin-5-yl)phenyl]oxazoline was obtained, 1.21 g, colorless crystals;

Workup

  1. temperaturerefluxed under nitrogen (7 hours)
  2. customAfter chromatography and recrystallization in heptane/ethyl acetate 95:5

Sources & evidence

ORD record
ord-971f3fcc961f4539a2a6153907271cd6
Source dataset
uspto-grants-2001_07
Patent number
US06265350B1

Reaction notes

Loading…