Dimethylformamide → HCID 178469533, compound

HRID 1581556Notes

Reaction equation

HRID 1581556 reaction equation
C(N(CC)CC)C.[CH2:8]([OH:11])[C:9]#[CH:10].Cl[C:13]1[N:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:16]2[OH:28].CN(C=O)C>CCOCC.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>[OH:28][C:16]1[C:15]2[C:20](=[CH:21][CH:22]=[C:13]([C:10]#[C:9][CH2:8][OH:11])[N:14]=2)[N:19]=[CH:18][C:17]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7859Propargyl alcohol2×HCID 8471TriethylamineHCID 178469542Ethyl 6-chloro-4-hydroxy[1,5]naphthyridine-3-carboxylate

Product 1

HCID 178469533HCID 178469533, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

Triethylamine (10 mL) is added to dry cuprous iodide (52 mg) under nitrogen. The mixture is stirred for 5 minutes. Propargyl alcohol (50 μL) is added. After stirring another 5 minutes, dichlorobis(triphenylphosphine)palladium(II) (48 mg) is added. The mixture is again stirred for 5 minutes before the addition of ethyl 6-chloro-4-hydroxy[1,5]naphthyridine-3-carboxylate (Preparation 1, 348 mg) and DMF (10 mL). After stirring another 5 minutes, the remaining propargyl alcohol (660 μL) is added, and the reaction is tightly capped and stirred at 70° C. for 11 hours. After cooling, the mixture is diluted with ether (75 mL), sonicated to break up any solids, and filtered. The collected solid is washed with ether, dried under vacuum and recrystallized from ethanol.

Workup

  1. stirringAfter stirring another 5 minutes
  2. stirringAfter stirring another 5 minutes
  3. customthe reaction is tightly capped
  4. stirringstirred at 70° C. for 11 hours
  5. temperatureAfter cooling
  6. customsonicated
  7. filtrationfiltered
  8. washThe collected solid is washed with ether
  9. customdried under vacuum
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a2aa1a35b2a0425eb280edcb0e610036
Source dataset
uspto-grants-2004_05
Patent number
US06730682B2

Reaction notes

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