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Ethyl chloroformate → 1h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(4-fluorophenyl)methyl]-3-[[2-(2-oxo-1-pyrrolidinyl)ethoxy]methyl]-,methyl ester

HRID 2377109
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Reaktionsgleichung

Reaktionsgleichung von HRID 2377109
CN([CH2:4][C:5]1[C:13]2[C:8](=[CH:9][N:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[N:7]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH:6]=1)C.ClC(OCC)=O.[OH:32][CH2:33][CH2:34][N:35]1[CH2:39][CH2:38][CH2:37][C:36]1=[O:40].C(N(C(C)C)C(C)C)C>C(Cl)Cl.CCOC(C)=O.CN(C=O)C>[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:7]2[C:8]3=[CH:9][N:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=[C:13]3[C:5]([CH2:4][O:32][CH2:33][CH2:34][N:35]3[CH2:39][CH2:38][CH2:37][C:36]3=[O:40])=[CH:6]2)=[CH:24][CH:23]=1
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Komponenten

8

Edukt 4

HCID 10928Ethyl chloroformateHCID 769801-(2-Hydroxyethyl)-2-pyrrolidinoneHCID 81531DiisopropylethylamineHCID 59855831HCID 59855831, Verbindung

Produkt 1

HCID 691986491h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(4-fluorophenyl)methyl]-3-[[2-(2-oxo-1-pyrrolidinyl)ethoxy]methyl]-,methyl esterAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirring solution of methyl 3-[(dimethylamino)methyl]-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (1.04 g, 3.05 mmol) in DCM (16 mL) under nitrogen was added ethyl chloroformate (0.330 g, 3.05 mmol). The solution was stirred for 2 hours at room temperature. At this time, 1-(2-hydroxyethyl)pyrrolidin-2-one (1.57 g, 12.18 mmol), ethyl(diisopropyl)amine (1.97 g, 15.23 mmol), and DMF (16 mL) were added to the reaction and the reaction heated to 55° C. After stirring for 24 hours (55° C.) the reaction was judged to be complete by HPLC-MS analysis and the volatiles were removed in vacuo (ca. 2 torr) to give red oil. The crude material was diluted with EtOAc (40 mL) and washed with water (4×20 mL) and brine (20 mL). The organic phase was separated, dried (Na2SO4), and concentrated in vacuo to afford the target compound, which was purified by chromatography on a column of silica gel. Fractions were combined to afford 0.961 g (76% yield) of methyl 1-(4-fluorobenzyl)-3-{[2-(2-oxopyrrolidin-1-yl)ethoxy]methyl}-1H-pyrrolo[2,3-c]pyridine-5-carboxylate as an off white solid. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.90-2.01 (m, 2H) 2.32 (t, J=8.10 Hz, 2H) 3.42-3.51 (m, 4H) 3.64 (t, J=5.27 Hz, 2H) 4.00 (s, 3H) 4.69 (s, 2H) 5.36 (s, 2H) 7.01 (t, J=8.57 Hz, 2H) 7.11-7.18 (m, 2H) 7.28 (s, 1H) 8.51 (s, 1H) 8.73 (s, 1H).

Aufarbeitung

  1. temperaturethe reaction heated to 55° C
  2. stirringAfter stirring for 24 hours (55° C.) the reaction
  3. customthe volatiles were removed in vacuo (ca. 2 torr)
  4. customto give red oil
  5. washwashed with water (4×20 mL) and brine (20 mL)
  6. customThe organic phase was separated
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customto afford the target compound, which
  10. customwas purified by chromatography on a column of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e930daf3165f4dd6822f64e3464bcc72
Quelldatensatz
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07468375B2

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