Sodium hydride → Ethyl 5-(2-methoxyethoxy)-1-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

HRID 553568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 553568
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[CH:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:12][C:9]2=[CH:10][N:11]=1.[H-].[Na+].C1(C)C=CC(S(O[CH2:32][CH2:33][O:34][C@@H:35]2[CH2:40][CH2:39][CH2:38][C@H:37]([O:41][CH2:42][C:43]3[N:44]=[C:45]([C:49]4[CH:50]=[C:51]([CH3:55])[CH:52]=[CH:53][CH:54]=4)[O:46][C:47]=3[CH3:48])[CH2:36]2)(=O)=O)=CC=1>CN(C=O)C.[Na+].[Cl-].C(OCC)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[CH:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:12]([CH2:32][CH2:33][O:34][CH:35]3[CH2:40][CH2:39][CH2:38][CH:37]([O:41][CH2:42][C:43]4[N:44]=[C:45]([C:49]5[CH:50]=[C:51]([CH3:55])[CH:52]=[CH:53][CH:54]=5)[O:46][C:47]=4[CH3:48])[CH2:36]3)[C:9]2=[CH:10][N:11]=1

Komponenten

7

Edukt 3

HCID 24758Sodium hydrideHCID 59820026(1R,3S)-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy)ethyl toluene-4-sulfonate2×HCID 59820057ethyl 5-(2-methoxyethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Produkt 1

HCID 67463595Ethyl 5-(2-methoxyethoxy)-1-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 5234Sodium ChlorideLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

66 mg of ethyl 5-(2-methoxyethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate are dissolved in 2 ml of dry DMF, and 12 mg of 60 percent strength sodium hydride suspension are added. After 30 min at room temperature, 100 mg of ((1R,3S)-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl toluene-4-sulfonate ((1R,3S)-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl toluene-4-sulfonate in 2 ml of DMF are added. The mixture is stirred at 40° C. until the reaction has gone to completion (monitored by LC-MS). After cooling, the mixture is diluted with sat. NaCl solution and ethyl acetate. The organic phase is dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is purified by flash chromatography on silica gel (n-heptane/ethyl acetate=1:2). This gives ethyl 5-(2-methoxyethoxy)-1-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-2-carboxylate as a yellowish solid. C33H41N3O7 (591.71), MS (ESI): 592 (M+H+).

Aufarbeitung

  1. temperatureAfter cooling
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customthe solvent is removed under reduced pressure
  4. customThe residue is purified by flash chromatography on silica gel (n-heptane/ethyl acetate=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-c25db0a84a71402f9a5aa029abfae9a2
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048901B2

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