Potassium Carbonate → HCID 178517029, compound

HRID 926524Notes

Reaction equation

HRID 926524 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[N:18][CH:19]=1)=[C:5]2[OH:20].Cl[C:22]([F:28])([F:27])C(OC)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([OH:12])[C:6]([CH2:13][C:14]1[CH:19]=[N:18][CH:17]=[N:16][CH:15]=1)=[C:5]2[O:20][CH:22]([F:28])[F:27]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 73935Methyl chlorodifluoroacetateHCID 1180061406-Bromo-4-hydroxy-3-(pyrimidin-5-ylmethyl)quinolin-2(1H)-one

Product 1

HCID 178517029HCID 178517029, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-bromo-4-hydroxy-3-(pyrimidin-5-ylmethyl)quinolin-2(1H)-one (0.5 g, 1.51 mmol, Intermediate 49: step a) methyl 2-chloro-2,2-difluoroacetate (0.24 mL, 2.26 mmol) and K2CO3 (0.52 mg, 3.76 mmol) in DMF (0.6 mL) was stirred at 80° C. for 2 hours, cooled to room temperature, diluted with H2O and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried, filtered, evaporated in-vacuo and purified by chromatography (0-10% MeOH in DCM, gradient) to provide the title compound.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated in-vacuo
  6. custompurified by chromatography (0-10% MeOH in DCM, gradient)

Sources & evidence

ORD record
ord-186a33564bbf4f7782be613da903a3d3
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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