Dimethylformamide → (5-Bromo-3-fluoro-pyridin-2-yl)-(4-methanesulfonyl-piperazin-1-yl)-methanone

HRID 873323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 873323
[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[CH3:11][S:12]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)(=[O:14])=[O:13].CN(C=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CC(O)=O.C(Cl)Cl.O>[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([CH2:8][N:18]2[CH2:19][CH2:20][N:15]([S:12]([CH3:11])(=[O:14])=[O:13])[CH2:16][CH2:17]2)=[N:6][CH:7]=1.[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([C:8]([N:18]2[CH2:19][CH2:20][N:15]([S:12]([CH3:11])(=[O:14])=[O:13])[CH2:16][CH2:17]2)=[O:9])=[N:6][CH:7]=1

Komponenten

9

Edukt 4

HCID 6228DimethylformamideHCID 7091611-(Methylsulfonyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 210758705-Bromo-3-fluoropyridine-2-carbaldehyde

Produkt 2

HCID 70978953(5-Bromo-3-fluoro-pyridin-2-yl)-(4-methanesulfonyl-piperazin-1-yl)-methanoneHCID 709790061-((5-Bromo-3-fluoropyridin-2-yl)methyl)-4-(methylsulfonyl)piperazine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-Bromo-3-fluoropicolinaldehyde (94 mg, 0.46 mmol) and 1-(methylsulfonyl)piperazine (82 mg, 0.5 mmol) were stirred in AcOH (0.11 mL) and DMF (1 mL) at rt. NaBH(OAc)3 (160 mg, 0.75 mmol) was added slowly and the reaction mixture stirred at room temperature for 3.5 h. Water and DCM were added and the aqueous phase was extracted with DCM. The combined organics were dried (MgSO4), filtered and concentrated in vacuo to give 1-((5-bromo-3-fluoropyridin-2-yl)methyl)-4-(methylsulfonyl)piperazine (Intermediate 7) as a colourless solid.

Aufarbeitung

  1. customat rt
  2. extractionthe aqueous phase was extracted with DCM
  3. dry with materialThe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3717887112de4eb4b05f5824001c6c05
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975406B2

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