Benzyl Bromide → 3-[Benzyl-(pyridine-3-sulfonyl)-amino]-benzoic acid

HRID 62817

Reaktionsgleichung

Reaktionsgleichung von HRID 62817
C([O:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][S:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH:8]=1)(C)(C)C.[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C.FC(F)(F)C(O)=O.ClCCl>[CH2:24]([N:13]([S:14]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)(=[O:15])=[O:16])[C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[C:6]([OH:5])=[O:23])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

7

Edukt 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 673108723-(Pyridine-3-sulfonylamino)-benzoic acid tert-butyl ester

Produkt 1

HCID 673107893-[Benzyl-(pyridine-3-sulfonyl)-amino]-benzoic acidAusbeute 53,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 21863450Trifluoroacetic acid methylene chlorideLösungsmittel

Versuchsvorschrift

A solution of 3-(Pyridine-3-sulfonylamino)-benzoic acid tert-butyl ester (99 mg, 0.3 mmol), benzyl bromide (39 μL, 0.32 mmol) and Cesium Carbonate (145 mg, 0.4 mmol) in dimethylformamide (5 ml) was stirred for 16 hrs. The reaction was diluted with ethyl acetate (50 ml) and washed with water (6×100 ml). The organic layer was separated, dried over magnesium sulfate and concentrated in vacuo to give a yellow oil. The oil was dissolved in trifluoroacetic acid/dichloromethane (1:5 v/v) (10 ml), stirred for 3 hrs and then concentrated in vacuo to afford the title compound as a white solid (58.7 mg). HPLC retention time 4.31 min. Mass spectrum (APCI+) m/z 369 (M+H).

Aufarbeitung

  1. washwashed with water (6×100 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a yellow oil
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-95c46d306a314f198fa1f310bd5902d8
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447033B2

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