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Potassium Carbonate → 5-Chloro-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-cyclopropylmethoxy-phenyl)-ethyl]-amide

HRID 855352
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HRID 855352 반응식
[C:1]([C:5]1[CH:33]=[CH:32][C:8]([CH2:9][N:10]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=2)[C:11]([C:13]2[CH:14]=[C:15]([Cl:22])[CH:16]=[C:17]3[C:21]=2[NH:20][CH:19]=[CH:18]3)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:41][CH:42]1[CH2:44][CH2:43]1>C(#N)C>[C:1]([C:5]1[CH:33]=[CH:32][C:8]([CH2:9][N:10]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:41][CH:42]3[CH2:44][CH2:43]3)[CH:26]=2)[C:11]([C:13]2[CH:14]=[C:15]([Cl:22])[CH:16]=[C:17]3[C:21]=2[NH:20][CH:19]=[CH:18]3)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 866030555-Chloro-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-hydroxy-phenyl)-ethyl]-amide

생성물 1

HCID 866030565-Chloro-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-cyclopropylmethoxy-phenyl)-ethyl]-amide

시약·촉매·용매 1

HCID 6342Acetonitrile
용매

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온도
80 °C

실험 절차

122 mg of 5-chloro-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-hydroxy-phenyl)-ethyl]-amide (0.25 mmol) and 52 mg potassium carbonate (0.375 mmol) were suspended in 5 ml acetonitrile and treated with 0.027 ml bromomethyl-cyclopropane (0.275 mmol). The mixture was stirred for 24 h in an oil-bath heated to 80° C. After cooling down, the mixture was poured on water/EtOAc, and after separation the aqueous phase was extracted with EtOAc. The combined organic phases were then washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silicagel, heptane/EtOAc 9:1) leading to 66 mg of 5-chloro-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-cyclopropylmethoxy-phenyl)-ethyl]-amide as a colorless viscous oil. MS (ISP) 515.5 (M+H)+.

후처리

  1. temperatureAfter cooling down
  2. additionthe mixture was poured on water/EtOAc
  3. customafter separation the aqueous phase
  4. extractionwas extracted with EtOAc
  5. washThe combined organic phases were then washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (8 g silicagel, heptane/EtOAc 9:1)

출처 및 근거

ORD 기록
ord-4475562d80bd47c68ccd736c04cd3673
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07259183B2

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