N,N-Diethyl-2-propanamine → [3-(3,4-Dimethoxy-phenyl)-pyrrolo[2,3-b]pyridin-1-yl]-(2-ethoxy-4-nitro-phenyl)-methanone

HRID 1820891

Reaktionsgleichung

Reaktionsgleichung von HRID 1820891
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(C(C)C)CC)C.[CH2:28]([O:30][C:31]1[CH:39]=[C:38]([N+:40]([O-:42])=[O:41])[CH:37]=[CH:36][C:32]=1[C:33](O)=[O:34])[CH3:29].F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([C:33]([C:32]3[CH:36]=[CH:37][C:38]([N+:40]([O-:42])=[O:41])=[CH:39][C:31]=3[O:30][CH2:28][CH3:29])=[O:34])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

6

Edukt 4

HCID 521913N,N-Diethyl-2-propanamineHCID 2733179PyBroPHCID 27363472-Ethoxy-4-nitrobenzoic acidHCID 116732853-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 57891702[3-(3,4-Dimethoxy-phenyl)-pyrrolo[2,3-b]pyridin-1-yl]-(2-ethoxy-4-nitro-phenyl)-methanoneAusbeute 77,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine 1(250 mg, 0.98 mmole) was dissolved in 50 mL of CH2Cl2. N,N-diethylisopropylamine (205 uL, 1.2 mmol), 2-ethoxy-4-nitro-benzoic acid (228 mg, 1.1 mmol) and bromotris(pyrolodino)phoshonium hexafluorophosphate (550 mg, 1.1 mmol) were added to the stirring reaction mixture. The mixture was stirred at ambient temperature for 4 h and washed consecutively with saturated sodium bicarbonate and saturated potassium bisulfate solution. The resulting solution was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (30% ethyl acetate in hexanes) to yield 340 mg (77%) of the titled compound as a yellow solid. MS(ESI) [M+H+]+=448.2.

Aufarbeitung

  1. washwashed consecutively with saturated sodium bicarbonate and saturated potassium bisulfate solution
  2. dry with materialThe resulting solution was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (30% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3a8ccfd22a4e4c6b98e6fdbdda52c2a2
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07605168B2

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