1-Chloro-4-(chloromethyl)benzene → Ethyl 1-(p-chlorobenzyl)-5-chloro-3-thiophenylindole-2-carboxylate

HRID 1090265

Reaktionsgleichung

Reaktionsgleichung von HRID 1090265
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]2[C:16]1[S:17][CH:18]=[CH:19][CH:20]=1.CC1C(C)=C(C)C(C)[SiH-](C)(C)C=1.[K+].[Cl:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39]Cl)=[CH:37][CH:36]=1.[Cl-].[NH4+]>O1CCCC1.C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOCC.CN(C)P(=O)(N(C)C)N(C)C>[Cl:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][N:7]2[C:8]3[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)[C:5]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)=[C:6]2[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:37][CH:36]=1

Komponenten

10

Edukt 4

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 25517Ammonium ChlorideHCID 67902874Ethyl 5-chloro-3-thiophenylindole-2-carboxylateHCID 131717145Potassium hexamethylsilamide

Produkt 1

HCID 67855865Ethyl 1-(p-chlorobenzyl)-5-chloro-3-thiophenylindole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 12679HexamethylphosphoramideLösungsmittel

Versuchsvorschrift

To a cold (78°), stirred solution containing 664 mg of ethyl 5-chloro-3-thiophenylindole -2-carboxylate from Preparation 5 in 3.5 mL of dry tetrahydrofuran, under argon, was added 3.5 mL of a 0.62M solution of potassium hexamethylsilamide in toluene. The reaction mixture was stirred at -78° for 1 h and at 0° for 1 h then recooled to -78°. 0.75 mL of p-chlorobenzyl chloride. 1.0 mL of hexamethylphosphoric triamide and 20 mg of tetra-n-butylammonium bromide were then added. The resultant mixture was allowed to warm to room temperature and stirred for 18 h. Saturated aqueous ammonium chloride and ether were added. The ether layer was separated, washed with water, 10% aqueous cupric sulfate, water and brine and dried over MgSO4.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at -78° for 1 h and at 0° for 1 h
  2. customthen recooled to -78°
  3. stirringstirred for 18 h
  4. customThe ether layer was separated
  5. washwashed with water, 10% aqueous cupric sulfate, water and brine
  6. dry with materialdried over MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-d7aaa2792f3c4a489604a471a7db3a0a
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05081138

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