Dichloromethane → 2-Methoxy-8-trimethylsilanylethynyl-[1,5]naphthyridine

HRID 1767040Notes

Reaction equation

HRID 1767040 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2OS(C(F)(F)F)(=O)=O.ClCCl.[CH3:24][Si:25]([C:28]#[CH:29])([CH3:27])[CH3:26]>C(N(CC)CC)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.Cl[Pd]Cl.[Cu]I>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([C:29]#[C:28][Si:25]([CH3:27])([CH3:26])[CH3:24])[CH:7]=[CH:8][N:9]=2)[N:4]=1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 66111TrimethylsilylacetyleneHCID 112552656-Methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonate

Product 1

HCID 211131562-Methoxy-8-trimethylsilanylethynyl-[1,5]naphthyridine

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

1,1,1-Trifluoro-methanesulfonic acid 6-methoxy-[1,5]naphthyridin-4-yl ester (10 g, 32 mmol) was partially dissolved in triethylamine (80 mL) and dichloromethane was added in small portions until solid was completely dissolved. The resulting solution was degassed and purged with nitrogen, then treated with (trimethylsilyl)acetylene (5 mL, 36 mmole), bis-(triphenylphosphine)palladium (II) chloride (456 mg, 0.65 mmole), and copper (I) iodide (125 mg, 0.65 mmol) at room temperature overnight. Reaction mixture was concentrated to near dryness, then redissolved in ethyl acetate and washed with water and brine. Insoluble material was filtered off and aqueous layer was dried over sodium sulfate, filtered and concentrated. The resulting brown thick oil was used without further purification.

Workup

  1. dissolutionwas completely dissolved
  2. customThe resulting solution was degassed
  3. custompurged with nitrogen
  4. customReaction mixture
  5. concentrationwas concentrated
  6. dissolutionredissolved in ethyl acetate
  7. washwashed with water and brine
  8. filtrationInsoluble material was filtered off
  9. dry with materialaqueous layer was dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe resulting brown thick oil was used without further purification

Sources & evidence

ORD record
ord-a44371ddb4e547aab530c1719b515fa5
Source dataset
uspto-grants-2007_06
Patent number
US07232832B2

Reaction notes

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