Ethanol → HCID 9932192, compound

HRID 971091Notes

Reaction equation

HRID 971091 reaction equation
[CH:1]([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=2)[CH:8]=1)=[O:6])([CH3:3])[CH3:2].[C:25]1(C)[CH:30]=[CH:29]C=[CH:27][CH:26]=1.[CH2:32]([OH:34])[CH3:33].[C:35](=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Br[Pd]Br>[CH:1]([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:26]3[CH:25]=[CH:30][CH:29]=[C:33]([C:32](=[O:34])[CH3:35])[CH:27]=3)[CH:19]=2)[CH:8]=1)=[O:6])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 1140TolueneHCID 10340Sodium CarbonateHCID 129913181-(3-bromophenyl)-N-isopropyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

Product 1

HCID 9932192HCID 9932192, compound

Reagents, catalysts & solvents 2

HCID 11104744HCID 11104744, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-Isopropyl-1-(3-bromophenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide from Step 4,3-acetylphenylboronic acid (1.2 eq.), trans-dibromobis(triphenylphosphine)palladium (II) (0.05 eq.), toluene (6 mL/mmol), ethanol (2 mL/mmol) and 2M aqueous sodium carbonate (8 eq.) was refluxed for 1 hour under a nitrogen atmosphere. The mixture was diluted with ethyl acetate and the organic phase was washed with water and brine, dried and evaporated. The crude product was chromatographed on silica gel eluting with a gradient of 20-40% ether in methylene chloride to afford the N-Isopropyl-1-[3-(3-acetylphenyl)phenyl]-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide product as a solid.

Workup

  1. temperaturewas refluxed for 1 hour under a nitrogen atmosphere
  2. washthe organic phase was washed with water and brine
  3. customdried
  4. customevaporated
  5. customThe crude product was chromatographed on silica gel eluting with a gradient of 20-40% ether in methylene chloride

Sources & evidence

ORD record
ord-d45e79cbeb2c44938e1440beabe26d82
Source dataset
uspto-grants-2007_12
Patent number
US07312334B2

Reaction notes

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