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

HRID 260477ノート

反応式

HRID 260477 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d888f10c1e12454e8ddab9396b718edd
出典データセット
uspto-grants-1996_06
特許番号
US05527819

反応ノート

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