2-(Tributylstannyl)furan → Ethyl 1-(2,4-dimethoxybenzyl)-6-fluoro-7-(2-furyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1696909Notes

Reaction equation

HRID 1696909 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([Sn](CCCC)(CCCC)[C:35]1[O:36][CH:37]=[CH:38][CH:39]=1)CCC>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[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:35]3[O:36][CH:37]=[CH:38][CH:39]=3)[N:11]=2)[C:6](=[O:28])[C:7]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:8]1

Participants

5

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 13937202Ethyl 7-chloro-1-(2,4-dimethoxybenzyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 67275183Ethyl 1-(2,4-dimethoxybenzyl)-6-fluoro-7-(2-furyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of Example 7F (210 mg), 2-(tributylstannyl)furan (220 μL) and dichlorobis(triphenyl-phosphine)palladium (II) (10.5 mg) in toluene (8 mL) was heated at 80° C. for 3 hours then cooled and filtered through diatomaceous earth (Celite®) with ethyl acetate. The filtrate was dried (Na2SO4), filtered, and concentrated; and the concentrate was flash chromatographed on silica gel with heptane then dichloromethane.

Workup

  1. temperaturethen cooled
  2. filtrationfiltered through diatomaceous earth (Celite®) with ethyl acetate
  3. dry with materialThe filtrate was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed on silica gel with heptane

Sources & evidence

ORD record
ord-a8643dcb8e1e443d8d92ab4ca2d3cd1a
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

Loading…