Dimethylformamide → 2-(4-chloro-phenyl)-3-formyl-1H-indole-4-carboxylic acid methyl ester

HRID 33336

Reaktionsgleichung

Reaktionsgleichung von HRID 33336
P(Cl)(Cl)(Cl)=O.CN([CH:9]=[O:10])C.[CH3:11][O:12][C:13]([C:15]1[C:16]2[CH:17]=[C:18]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[NH:19][C:20]=2[CH:21]=[CH:22][CH:23]=1)=[O:14]>C(Cl)Cl>[CH3:11][O:12][C:13]([C:15]1[C:16]2[C:17]([CH:9]=[O:10])=[C:18]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[NH:19][C:20]=2[CH:21]=[CH:22][CH:23]=1)=[O:14]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 183400022-(4-Chloro-phenyl)-1H-indole-4-carboxylic acid methyl ester

Produkt 1

HCID 183400032-(4-chloro-phenyl)-3-formyl-1H-indole-4-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Phosphorous oxychloride (0.42 g, 2.71 mmol) was added to DMF (0.99 g, 13.57 mmol) at 0° C. The resulting colorless solution was added dropwise to a solution of 2-(4-chloro-phenyl)-1H-indole-4-carboxylic acid methyl ester (0.52 g, 1.81 mmol) in 10 mL dry CH2Cl2 at 0° C. The reaction was stirred at 0° C. for 10 min then quenched by addition of 5 mL 2 M NaOAc(aq). The layers were separated and the aqueous layer extracted once with CH2Cl2. The combined organic layers were dried (MgSO4) then concentrated in vacuo leaving anorange oil which crystallized on standing. The crystals were rinsed with CH2Cl2 then dried in vacuo to yield 2-(4-chloro-phenyl)-3-formyl-1H-indole-4-carboxylic acid methyl ester, 231 mg (41%) as an off-white solid: m.p. 221-222° C.; 1H NMR (300 MHz, d6-DMSO) δ 3.93 (s, 3H), 7.49 (app t, J=7.5 Hz, 1H), 7.71 (m, 4H), 7.94 (d, J=7.8 Hz, 2H), 9.71 (s, 1H), 13.67 (br s, 1H). MS (electrospray, [M−H]) 312.

Aufarbeitung

  1. customthen quenched by addition of 5 mL 2 M NaOAc(aq)
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted once with CH2Cl2
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationthen concentrated in vacuo
  6. customleaving anorange oil which
  7. customcrystallized
  8. washThe crystals were rinsed with CH2Cl2
  9. customthen dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5395efbbbbf94486a8c3769c04995d3e
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429578B2

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