Boron trifluoride etherate → ethyl 5-chloro-3-(phenylthio)-1H-indole-2-carboxylate

HRID 260477노트

반응식

HRID 260477 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])=[CH:5]2.[C:16]1([S:22]N2C(=O)CCC2=O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.B(F)(F)F.CCOCC>C(Cl)Cl.C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>[C:16]1([S:22][C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=3)[NH:7][C:6]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

7

반응물 3

HCID 8000Boron trifluoride etherateHCID 78518Ethyl 5-chloroindole-2-carboxylateHCID 3617741-(Phenylthio)pyrrolidine-2,5-dione

생성물 1

HCID 15035363ethyl 5-chloro-3-(phenylthio)-1H-indole-2-carboxylate

시약·촉매·용매 3

HCID 6212Chloroform용매HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a partial suspension of ethyl 5-chloroindole-2-carboxylate (698 mg, 3.1 mmol) and N-(phenylthio)succinimide (683 mg, 3.3 mmol) in anhydrous methylene chloride (20 mL) at ambient temperature under an inert gas atmosphere was added boron trifluoride etherate (0.12 mL, 1.0 mmol). The reaction was monitored by tlc (thin layer chromatography) until complete. After 2 hours, the reaction was diluted with chloroform and neutralized with aq. NaHCO3. The organic layer was dried (Na2SO4), filtered through a pad of charcoal, and the solvents evaporated. The residue was triturated with hexanes as the product crystallized out to yield the title product, mp 160°-162° C. [see Table II, mp 163°-164° C⟧ This material was used as is.

후처리

  1. dry with materialThe organic layer was dried (Na2SO4)
  2. filtrationfiltered through a pad of charcoal
  3. customthe solvents evaporated
  4. customThe residue was triturated with hexanes as the product
  5. customcrystallized out

출처 및 근거

ORD 기록
ord-d888f10c1e12454e8ddab9396b718edd
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05527819

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