6-Bromoquinoline → HCID 15859257, compound

HRID 1292420Notes

Reaction equation

HRID 1292420 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:12]2[CH2:16][CH:15]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[O:14][C:13]2=[O:22])[CH:5]=[CH:6][C:7]=1[Sn](C)(C)C.Br[C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[N:30]=[CH:29][CH:28]=[CH:27]2>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([N:12]2[CH2:16][CH:15]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[O:14][C:13]2=[O:22])[CH:5]=[CH:6][C:7]=1[C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[N:30]=[CH:29][CH:28]=[CH:27]2

Participants

5

Reactant 2

HCID 792436-BromoquinolineHCID 15859258HCID 15859258, compound

Product 1

HCID 15859257HCID 15859257, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

(±)-N-[[3-[3-fluoro-4-(trimethylstannyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (PREPARATION 19, 0.367 g, 0.88 mmol), 6-bromoquinoline (0.239 g, 1.15 mmol) and bis(triphenyl-phosphine)palladium(II) chloride (0.062 g, 0.088 mmol) are combined with DMF (10 ml). The reaction mixture is thoroughly purged with nitrogen and then heated to 80° under nitrogen. After 2 hr, little progress is noted by TLC and so the reaction mixture is heated to 95° for a further 2 hr. At this point, TLC revealed the reaction is complete. The mixture is cooled to 20°-25° and concentrated under reduced pressure to give a crude material which is purified by chromatography over silica gel (10 g of silica gel; eluted with methanol/chloroform, 1→4%) to give the racemic title compound, mp 216°-219° (dec); IR (internal reflectance) 3411, 3281, 1743, 1657, 1630, 1566, 1521, 1499, 1416, 1226, 1194 cm-1 ; NMR (CDCl3, 300 MHz) 8.95, 8.26-8.20, 8.00, 7.92, 7.61, 7.57, 7.47, 7.35, 6.08, 4.84, 4.13, 3.86, 3.80-3.62, 2.05 δ;MS (m/z) 379 (100.0, M+), 335, 307, 276, 264, 251.

Workup

  1. customThe reaction mixture is thoroughly purged with nitrogen
  2. temperatureheated to 80° under nitrogen
  3. temperatureis heated to 95° for a further 2 hr
  4. temperatureThe mixture is cooled to 20°-25°
  5. concentrationconcentrated under reduced pressure
  6. customto give a crude material which
  7. customis purified by chromatography over silica gel (10 g of silica gel; eluted with methanol/chloroform, 1→4%)

Sources & evidence

ORD record
ord-a467e5487f834a44a8bcc89e5d562a00
Source dataset
uspto-grants-1998_05
Patent number
US05756732

Reaction notes

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