Propargyl bromide → HCID 19025378, compound

HRID 1033167Notes

Reaction equation

HRID 1033167 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]1=[O:24])[NH:8][C:7](=[O:25])[C:6]([C:26]([F:29])([F:28])[F:27])=[CH:5]2.Br[CH2:31][C:32]#[CH:33].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:33]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([F:1])=[C:11]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=2)[CH:5]=[C:6]([C:26]([F:29])([F:27])[F:28])[C:7]1=[O:25])[C:32]#[CH:31]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 19025374HCID 19025374, compound

Product 1

HCID 19025378HCID 19025378, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

These compounds were prepared in a manner analogous to that of Step I of Example 1, using 1.0 gram (0.002 mole) of 3-(6-fluoro-3-trifluoromethylquinolin-2-on-7-yl)-1-methyl-6-trifluoromethyluracil, 0.7 gram (0.005 mole) of 80% 3-bromopropyne, and 0.7 gram (0.005 mole) of potassium carbonate in 40 mL of N,N-dimethylformamide. The crude reaction product was subjected to column chromatography on silica gel. Elution was accomplished using 1:4 ethyl acetate-hexane and 1:1 ethyl acetatehexane. The appropriate product-containing fractions were combined and concentrated under reduced pressure, yielding 0.8 gram of 3-[1-(2-propyn-1-yl)-3-trifluoromethyl-6-fluoroquinolin-2-on-7-yl]-1-methyl-6-trifluoromethyluracil (Compound 42), mp 248°-250° C. Other product-containing fractions were combined and concentrated under reduced pressure, yielding 0.1 gram of the O-alkylated product, 3-[2-(2-propyn-1-yloxy)-3-trifluoromethyl-6-fluoroquinolin-2-on-7-yl]-1-methyl-6-trifluoromethyluracil (Compound 26A). The NMR spectra were consistent with the proposed structures.

Workup

  1. customThese compounds were prepared in a manner analogous to that of Step I of Example 1
  2. customThe crude reaction product
  3. washElution
  4. additionThe appropriate product-containing fractions
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-814c7bd4a6454660b5c6dced32928282
Source dataset
uspto-grants-1994_05
Patent number
US05310723

Reaction notes

Loading…