Triethylamine → 2-(1-BOC-2-(S)-pyrrolidinyl)furo[3,2-b]pyridine

HRID 611554

Reaktionsgleichung

Reaktionsgleichung von HRID 611554
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]#[CH:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.I[C:23]1[C:28]([OH:29])=[CH:27][CH:26]=[CH:25][N:24]=1>CN(C=O)C.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.[Cu]I>[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[O:29][C:28]2[C:23](=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

8

Edukt 3

HCID 8471TriethylamineHCID 971792-Iodopyridin-3-olHCID 11030701(S)-N-Boc-2-ethynylpyrrolidine

Produkt 1

HCID 153897342-(1-BOC-2-(S)-pyrrolidinyl)furo[3,2-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A 2.34 g (12 mmol) sample of the compound from step 1c above was dissolved in 15 mL of DMF, and (Ph3P)2PdCl2 (0.6 mmol), CuI (0.74 mmol) and triethylamine (14.25 mmol) were added. The mixture was stirred at room temperature for 1 hour, then 3.14 g (14.4 mmol) of 2-iodo-3-hydroxypyridine (Lancaster Chem. Co.) was added. The reaction mixture was stirred at 60° C. for 16 hours. The solution was cooled, diluted with toluene, and the volatiles were removed under reduced pressure. The residue was dissolved in 1 N HCl, and this solution was extracted with ether. The acidic aqueous layer was adjusted to pH 10 with K2CO3, and this solution was extracted with CH2Cl2. The CH2Cl2 extract was washed with 20% Na,OH, dried over MgSO4, and evaporated. The residue was chromatographed on silica gel, eluting with 100:0 to 95:5 CHCl3 :MeOH to give 980 mg of title compound: 1H NMR (CDCl3, 300 MHz) δ 1.32 (s, 9H), 1.90-2.20 (m, 4H), 2.95-3.15 (m, 2H), 5.05 (m, 1H), 6.68 (s, 1H), 7.15 (br s, 1H), 7.67 (d, 1H, J=8 Hz), 8.48 (d, 1H, J=3 Hz); MS m/z: 289 (M+H)+.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at 60° C. for 16 hours
  2. temperatureThe solution was cooled
  3. customthe volatiles were removed under reduced pressure
  4. dissolutionThe residue was dissolved in 1 N HCl
  5. extractionthis solution was extracted with ether
  6. extractionthis solution was extracted with CH2Cl2
  7. extractionThe CH2Cl2 extract
  8. washwas washed with 20% Na,OH
  9. dry with materialdried over MgSO4
  10. customevaporated
  11. customThe residue was chromatographed on silica gel
  12. washeluting with 100:0 to 95:5 CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-252b0b72149540b6b29b0f947b513751
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06001849

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