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Potassium Hydroxide → 1-(6-Chloronaphth-2-ylsulphonyl)-4-[4-(3-pyridyl)benzoyl]piperazine

HRID 379560
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 379560
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:29])[C:22]3[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=3)[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.C(B(CC)[C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1)C.[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.CCOC(C)=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:29])[C:22]3[CH:27]=[CH:26][C:25]([C:33]4[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=4)=[CH:24][CH:23]=3)[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2
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Komponenten

8

Edukt 3

HCID 14797Potassium HydroxideHCID 6428513-(Diethylboryl)pyridineHCID 223297181-(6-Chloronaphth-2-ylsulphonyl)-4-(4-iodobenzoyl)piperazine

Produkt 1

HCID 120510341-(6-Chloronaphth-2-ylsulphonyl)-4-[4-(3-pyridyl)benzoyl]piperazineAusbeute 38,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 74236
Tetrabutylammonium Bromide
Katalysator
HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysator
HCID 8028TetrahydrofuranLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-(6-Chloronaphth-2-ylsulphonyl)-4-(4-iodobenzoyl)piperazine (920 mg, 1.7 mmol), diethyl 3-pyridylborane (250 mg, 1.7 mmol), tetrabutyl ammonium bromide (110 mg, 0.34 mmol), tetrakis(triphenylphosphine) palladium (0) (69 mg,0.06 mmol) and potassium hydroxide (286 mg, 5.1 mmol) were refluxed in dry tetrahydrofuran (100 mL) for two hours under an atmosphere of nitrogen. The reaction mixture was allowed to cool to room temperature then concentrated in vacuo. The resulting solid was subjected to flash chromatography (SiO2: 100% CH2Cl2, 50% EtOAc/Hexane, 100% EtOAc) to yield an oil. The oil was dissolved in EtOAc (100 mL) and washed with saturated sodium hydrogen carbonate solution (100 mL). The EtOAc layer was separated, dried over MgSO4, filtered and concentrated in vacuo to yield an off white foam which was triturated with hexane. This solid was subjected to chromatography (SiO2: 40%, 50%, 60%, 70% EtOAc/Hexane) to yield 1-(6-chloronaphth-2-ylsulphonyl)-4-[4-(3-pyridyl)benzoyl]piperazine as a white solid (322.4 mg); 1H NMR (DMSO-d6) δ=3.1 ppm (s,4H), δ=3.6 ppm (s,4H), δ=7.46 ppm (d,2H), δ=7.5 to 7.67 ppm (m,1H), δ=7.70 to 7.79 ppm (m,3H), δ=7.83 ppm (dd,1H), δ=8.09 ppm (dt,1H), δ=8.15 ppm to 8.31 ppm (m,3H), δ=8.50 ppm (s,1H), δ=8.60 ppm (dd,1H), δ=8.90 ppm (d,1H); MS (M+H)+ 492.

Aufarbeitung

  1. concentrationthen concentrated in vacuo
  2. customto yield an oil
  3. washwashed with saturated sodium hydrogen carbonate solution (100 mL)
  4. customThe EtOAc layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto yield an off white foam which
  9. customwas triturated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-4135ce9b1b82411fb14e31e31be7d92b
Quelldatensatz
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06300330B1

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