Chloroform → HCID 57815172, compound

HRID 385567Notes

Reaction equation

HRID 385567 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:18])[N:9]2[CH2:12][CH:13]2[O:17][CH2:16][CH2:15][O:14]2)=[N:4][CH:3]=1.[C:19](=[O:26])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[NH2:20].C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)(Cl)Cl>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.O>[O:14]1[CH2:15][CH2:16][O:17][CH:13]1[CH2:12][N:9]1[C:8](=[O:18])[CH:7]=[CH:6][C:5]2[N:4]=[CH:3][C:2]([NH:20][C:19](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:11][C:10]1=2

Participants

9

Reactant 4

HCID 6212ChloroformHCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 578153037-bromo-1-(1,3-dioxolan-2-ylmethyl)-1,5-naphthyridin-2(1H)-one

Product 1

HCID 57815172HCID 57815172, compoundYield 64.9%

Reagents, catalysts & solvents 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
92.5 °C

Procedure

To a suspension of 0.40 g of 7-bromo-1-((1,3-dioxolan-2-yl)methyl)-1,5-naphthyridin-2(1H)-one in 4 mL of dioxane, 0.18 g of tert-butyl carbamate, 0.59 g of cesium carbonate, 22 mg of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, and 18 mg of tris(dibenzylideneacetone)dipalladium(0) were added at room temperature, and the mixture was stirred at 90 to 95° C. for 4 hour 15 minutes. After cooling to the room temperature, chloroform and water were added to the reaction mixture, the organic layer was separated, and washed with water and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, diethyl ether was added to the resultant residue and the solid was filtered off to obtain 0.29 g of tert-butyl (5-(1,3-dioxolan-2-yl)methyl-6-oxo-5,6-dihydro-1,5-naphthyridin-3-yl)carbamate as a light yellow solid.

Workup

  1. additionwere added at room temperature
  2. additionwere added to the reaction mixture
  3. customthe organic layer was separated
  4. washwashed with water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure, diethyl ether
  7. additionwas added to the resultant residue
  8. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-4817055c10fc4f24840a8730b3a72a7e
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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