Triethylamine → Methyl 3-(3,4-Difluorobenzylcarbamoyl)-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylate

HRID 40100

Reaktionsgleichung

Reaktionsgleichung von HRID 40100
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:23]([OH:25])=O)=[C:8]([C:19]([O:21][CH3:22])=[O:20])[N:9]2[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:5][CH:4]=1.C(Cl)(C(Cl)=O)=O.[F:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][C:40]=1[F:41])[CH2:36][NH2:37].CCN(CC)CC>C(Cl)Cl.CN(C=O)C.CCOC(C)=O>[F:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][C:40]=1[F:41])[CH2:36][NH:37][C:23]([C:7]1[C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:8]=1[C:19]([O:21][CH3:22])=[O:20])=[O:25]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1235723,4-DifluorobenzylamineHCID 597623576-Methoxy-2-(methoxycarbonyl)-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxylic Acid2×

Produkt 1

HCID 59762310Methyl 3-(3,4-Difluorobenzylcarbamoyl)-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 6-methoxy-2-(methoxycarbonyl)-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxylic acid (Compound 92, 1.59 g, 4.7 mmol) in anhydrous CH2Cl2 (50 ml) was added DMF (3 drops, catalytic amount) and (COCl)2 (2M in CH2Cl2, 5.9 ml, 11.8 mmol). The resulting mixture was stirred at room temperature for 1 h, and was concentrated in vacuo. To a solution of the crude product in CH2Cl2 (50 ml) was added 3,4-difluorobenzylamine (0.84 ml, 7.05 mmol), followed by Et3N (2.0 ml, 14.1 mmol). The reaction was stirred at room temperature for 1 h, diluted with EtOAc, washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes) to yield the title compound as a white solid.

Aufarbeitung

  1. concentrationwas concentrated in vacuo
  2. stirringThe reaction was stirred at room temperature for 1 h
  3. washwashed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-21500f5beb23491a83ce2c5100e1d2b2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524917B2

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