Benzoyl chloride → HCID 9797761, Verbindung

HRID 367372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 367372
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[C:20]1[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH:25]=1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[C:1]([N:16]1[C:17]2[C:13](=[CH:12][C:11]([F:10])=[CH:19][CH:18]=2)[C:14]([C:20]2[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH:25]=2)=[CH:15]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 149732095-fluoro-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole

Produkt 1

HCID 9797761HCID 9797761, VerbindungAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Benzoyl chloride (33.3 mg, 0.24 mmol) was added to a solution of 5-fluoro-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)indole (Example 4b, 49.6 mg, 0.215 mmol), triethylamine (0.15 mL, 1.1 mmol) and DMAP (5 mg) in dichloromethane (2 mL). The mixture was stirred at room temperature prior to quenching with water and extraction into dichloromethane. The organic layer was washed with brine and dried over sodium sulfate. Purification by flash chromatography (silica gel, 2M methanolic ammonia in chloroform) yielded 1-benzoyl-5-fluoro-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)indole (27.8 mg, 39%, HRMS-FAB+ for C21H20N2OF calculated MH+ : 335.15598; found: 335.15457).

Aufarbeitung

  1. customto quenching with water and extraction into dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customPurification by flash chromatography (silica gel, 2M methanolic ammonia in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-f4c6370d1b644e638da2e3eb9a5342df
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133287

Notizen zur Reaktion

Wird geladen…