Potassium Carbonate → HCID 54741167, compound

HRID 878387Notes

Reaction equation

HRID 878387 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10]1[C:11](=[O:27])[NH:12][C:13]2[C:18]([C:19]=1[O:20]C(=O)C(C)(C)C)=[CH:17][CH:16]=[CH:15][N:14]=2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][CH:36]([F:38])[F:37]>CN(C)C=O>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10]1[C:11](=[O:27])[N:12]([CH2:35][CH:36]([F:38])[F:37])[C:13]2[C:18]([C:19]=1[OH:20])=[CH:17][CH:16]=[CH:15][N:14]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1361862-Bromo-1,1-difluoroethaneHCID 58133379HCID 58133379, compound

Product 1

HCID 54741167HCID 54741167, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2,2-dimethyl-propionic acid 3-(2-chloro-3,6-difluoro-phenyl)-2-oxo-1,2-dihydro-[1,8]naphthyridin-4-yl ester (Example 1.5) (0.2 g), potassium carbonate (0.211 g) and 1-bromo-2,2-difluoro-ethane (0.15 g) in N,N-dimethylformamide (3 ml) was heated to 120° C. in a microwave for 15 minutes. The reaction mixture was partitioned between ethyl acetate and water. The phases were separated and the organic phase was dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane 1:1) to give Compound No. D21 of Table D as a colourless oil (24 mg).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe phases were separated
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane 1:1)
  6. customto give Compound No

Sources & evidence

ORD record
ord-5985023bb669424f9dcf2d00ca70d2e9
Source dataset
uspto-grants-2015_03
Patent number
US08987455B2

Reaction notes

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