Potassium Acetate → Ethyl 1-(2,4-dimethoxybenzyl)-6-fluoro-7-(3-fluorophenyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1696912Notes

Reaction equation

HRID 1696912 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:28])[C:7]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:8][N:9]2[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[O:21][CH3:22])=[CH:4][C:3]=1[F:29].C([O-])(=O)C.[K+].[F:35][C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][CH:41]=1>CN(C=O)C.ClCCl>[CH3:22][O:21][C:14]1[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=1[CH2:12][N:9]1[C:10]2[C:5](=[CH:4][C:3]([F:29])=[C:2]([C:40]3[CH:39]=[CH:38][CH:37]=[C:36]([F:35])[CH:41]=3)[N:11]=2)[C:6](=[O:28])[C:7]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:8]1

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 27339863-Fluorophenylboronic acidHCID 13937202Ethyl 7-chloro-1-(2,4-dimethoxybenzyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 67275331Ethyl 1-(2,4-dimethoxybenzyl)-6-fluoro-7-(3-fluorophenyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of EXAMPLE 7F (210 mg), potassium acetate (176 mg), 3-fluorobenzeneboronic acid (84 mg), and (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium (II) (12 mg) in DMF (6 mL) was heated at 90° C. for 3 hours then cooled, diluted with dichloromethane, washed with water, and dried (Na2SO4), filtered, and concentrated; and the concentrate was flash chromatographed on silica gel with 0-2% methanol/dichloromethane.

Workup

  1. temperaturethen cooled
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed on silica gel with 0-2% methanol/dichloromethane

Sources & evidence

ORD record
ord-34d661efe2a94066a55063a0b922053c
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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