HCID 90047122, compound → HCID 131734343, compound

HRID 1505005Notes

Reaction equation

HRID 1505005 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]=[C:10]2[C:15](=[O:16])OC(C)(C)OC2=O)=[CH:4][C:3]=1[F:20]>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[F:20])[NH:8][CH:9]=[CH:10][C:15]2=[O:16].[Br:1][C:2]1[C:3]([F:20])=[C:4]2[C:5](=[CH:6][CH:7]=1)[NH:8][CH:9]=[CH:10][C:15]2=[O:16]

Participants

3

Reactant 1

HCID 90047122HCID 90047122, compound

Product 1

HCID 131734343HCID 131734343, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Conditions

Temperature
245 °C

Procedure

5-(((4-Bromo-3-fluorophenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (61.14 g, 177.6 mmol) was added portion-wise to Dowtherm (270 mL) at 245° C. After the addition, stirred at 245° C. for 20 minutes. Cool to RT. Added hexanes (˜830 mL) and filtered the solid washing with additional hexanes and dried the solid to yield 6-bromo-7-fluoroquinolin-4(1H)-one/6-bromo-5-fluoroquinolin-4(1H)-one (38.02 g, 88.5%) as brown solid and as a mixture of regioisomers (46:54, by LCMS). MS: m/z: 242.0/244.0 [M+H]+. Used this mixture as is for the next step.

Workup

  1. additionAfter the addition
  2. temperatureCool to RT
  3. filtrationAdded hexanes (˜830 mL) and filtered the solid
  4. washwashing with additional hexanes
  5. customdried the solid

Sources & evidence

ORD record
ord-6dede457f63c460d80d71c215f2e8449
Source dataset
uspto-grants-2015_12
Patent number
US09216965B2

Reaction notes

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