Pyridine → 4-(6-tert-Butyl-5-thiocyanato-2,3-dihydro-indole-1-sulfonyl)-benzonitrile

HRID 1859553

반응식

HRID 1859553 반응식
[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][NH:11]2)=[CH:7][C:6]=1[S:14][C:15]#[N:16])([CH3:4])([CH3:3])[CH3:2].[C:17]([C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1)#[N:18].N1C=CC=CC=1>C(Cl)Cl>[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][N:11]2[S:25]([C:22]2[CH:21]=[CH:20][C:19]([C:17]#[N:18])=[CH:24][CH:23]=2)(=[O:27])=[O:26])=[CH:7][C:6]=1[S:14][C:15]#[N:16])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 225729956-tert-butyl-5-thiocyanato-2,3-dihydro-1H-indole

생성물 1

HCID 225730724-(6-tert-Butyl-5-thiocyanato-2,3-dihydro-indole-1-sulfonyl)-benzonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

6-tert-Butyl-5-thiocyanato-2,3-dihydro-1H-indole (prepared in Example JJ; 4.5 g, 19 mmol) was taken in CH2Cl2 (50 mL) and treated with 4-cyanophenylsulfonyl chloride (3.91 g, 19.4 mmol) and pyridine (5 mL). The reaction mixture was stirred overnight, quenched with saturated NaHCO3 solution, and diluted with EtOAc. The organic layer was separated, dried (MgSO4), and concentrated. The crude product was purified by flash chromatography (20%-75% EtOAc in hexanes as eluents). MS(APCI): 397 (M+).

후처리

  1. customquenched with saturated NaHCO3 solution
  2. additiondiluted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (20%-75% EtOAc in hexanes as eluents)

출처 및 근거

ORD 기록
ord-46eeb404b3694e09b91016268c49b9fd
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06528510B1

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