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Ammonium Chloride → 3-(2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione

HRID 639195
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 639195
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:12][N:13]([CH3:15])[CH3:14])[CH:8]=2)[C:3]=1[CH2:16][C:17]([NH2:19])=[O:18].C[O:21][C:22](=O)[C:23]([C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]([CH3:34])[CH:26]=1)=O.CC([O-])(C)C.[K+].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:12][N:13]([CH3:14])[CH3:15])[CH:8]=2)[C:3]=1[C:16]1[C:17](=[O:18])[NH:19][C:22](=[O:21])[C:23]=1[C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]([CH3:34])[CH:26]=1
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Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 44536752-(1-Methyl-1H-indol-3-YL)-2-oxoacetic acid methyl esterHCID 23665647Potassium tert-butoxideHCID 687039782-(2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)acetamide

Produkt 1

HCID 112016113-(2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Activated 3 Å molecular sieve (50 mg) is added to a solution of 2-(2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)acetamide (54.6 mmol, 0.20 mmol) and (1-Methyl-1H-indol-3-yl)-oxo-acetic acid methyl ester (55.7 mg, 0.26 mmol) in dry THF (2.5 ml) under an atmosphere of argon. A solution of 1.0 M KOtBu in THF (0.59 ml, 0.59 mmol) is then added in one portion at RT. After 30 minutes at RT, TLC analysis indicates complete conversion of starting materials. The reaction mixture is diluted with EtOAc and poured into a saturated aqueous NH4Cl solution. The organic layer is separated, washed with brine, dried over Na2SO4, and the organic solvent is evaporated. The residue is purified by FCC (EtOAc/AcOH/H2O 700:110:90) to afford the title compound. 1H NMR (d6-DMSO, 400 MHz): δ 2.12 (s, 6H), 3.46 (s, 2H), 3.82 (s, 3H), 6.16 (d, J=8.8 Hz, 1H), 6.45-6.51 (m, 1H), 6.96-7.02 (m, 1H), 7.32-7.40 (m, 2H), 7.60-7.68 (m, 2H), 7.88 (s, 1H), 8.06 (d, J=10 Hz, 1H), 8.15 (s, 1H). ES+-MS: 445.5, 446.6 [M+H]+.

Aufarbeitung

  1. customThe organic layer is separated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customthe organic solvent is evaporated
  5. customThe residue is purified by FCC (EtOAc/AcOH/H2O 700:110:90)

Quellen und Nachweise

ORD-Eintrag
ord-0a20c0f650004e24a42ed79a3a37afaa
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07691861B2

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