Triethylamine → 1-Benzyl-4-(2,2-dimethyl-propionyloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 642413
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:22])=[C:8]2[CH:14]=[CH:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].[C:23](Cl)(=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[C:8]2[CH:14]=[CH:13][N:12]([CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 684277721-Benzyl-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Produkt 1

HCID 684273231-Benzyl-4-(2,2-dimethyl-propionyloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl esterAusbeute 93,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1-benzyl-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (500 mg, 1.68 mmol), pivaloyl chloride (0.250 mL, 2.02 mmol), 4-dimethylaminopyridine (21 mg, 0.168 mmol) and triethyl amine (0.468 mL, 3.36 mmol) in dichloromethane (5 mL) was stirred at room temperature for 1 h; then the reaction mixture was diluted with EtOAc, washed with saturated NaCl solution and subsequently the organic phase was dried over anhydrous sodium sulfate, filtered, concentrated and the residue was purified with column to give the desired product as a clear oil (599 mg, 93%). 1H NMR (200 MHz, CDCl3): δ (ppm)=8.62 (s, 1H), 7.31-7.20 (m, 6H), 6.53-6.51 (m, 1H), 5.40 (s, 2H), 4.41 (q, 2H, J=7.3 Hz), 1.47 (s, 9H), 1.41 (t, 3H, J=7.3 Hz).

Aufarbeitung

  1. washwashed with saturated NaCl solution
  2. dry with materialsubsequently the organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified with column

Quellen und Nachweise

ORD-Eintrag
ord-c21011174c7e44b4925144cbacb27c14
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696223B2

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