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

HRID 483406

반응식

HRID 483406 반응식
[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

참가 물질

10

반응물 4

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

생성물 1

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

시약·촉매·용매 5

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 12679Hexamethylphosphoramide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c149c78e537a4b2aaf0a44152e4574ab
출처 데이터셋
uspto-grants-1993_07
특허 번호
US05225421

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