Benzal chloride → Ethyl 1-(p-chlorobenzyl)-5-chloro-3-thiophenylindole-2-carboxylate

HRID 483406

Reaction equation

HRID 483406 reaction equation
[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.C[C:22]1[C:23](C)=[C:24]([CH3:31])[CH:25]([CH3:30])[SiH-](C)(C)[CH:27]=1.[K+].[Cl:34]C(Cl)C1C=CC=CC=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:27]1[CH:22]=[CH:23][C:24]([CH2:31][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:25][CH:30]=1

Participants

10

Reactant 4

HCID 7411Benzal chlorideHCID 25517Ammonium ChlorideHCID 67902874Ethyl 5-chloro-3-thiophenylindole-2-carboxylateHCID 131717145Potassium hexamethylsilamide

Product 1

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

Reagents, catalysts & solvents 5

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

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 0.62 M 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 g 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.

Workup

  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

Sources & evidence

ORD record
ord-c149c78e537a4b2aaf0a44152e4574ab
Source dataset
uspto-grants-1993_07
Patent number
US05225421

Linked notes

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