2-Mesitylenesulfonyl chloride → 2,4,6-Trimethyl-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamide

HRID 18501

반응식

HRID 18501 반응식
[F:1][C:2]([F:16])([F:15])[CH:3]([NH2:14])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.[C:17]1([CH3:29])[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:18]=1[S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1.Cl>[CH3:29][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:18]=1[S:25]([NH:14][CH:3]([CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)[C:2]([F:1])([F:15])[F:16])(=[O:26])=[O:27]

참가 물질

5

반응물 2

HCID 130462-Mesitylenesulfonyl chlorideHCID 539884361,1,1-trifluoro-3-(1H-indol-3-yl)propan-2-amine2회

생성물 1

HCID 116829892,4,6-Trimethyl-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamide수율 67%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 1049Pyridine용매

반응 조건

온도
45 °C

실험 절차

A mixture of 42 mg (0.18 mmol) of 2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethylamine and 45 mg, 0.21 mmol) of mesitylenesulfonyl chloride in 0.5 mL of pyridine was warmed to 45° C. The reaction was monitored by thin layer chromatography (ethyl acetate-hexanes (3:7)) indicating a new less polar product compared to the amine. After 6 hours, the mixture was cooled and diluted with 7 mL of 1 N aqueous HCl and extracted with three 7 mL portions of ethyl acetate. The combined organic layers were washed with three 5 mL portions of 1 N aqueous HCl, 5 mL of brine, three 5 mL portions of saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 62 mg (82.1%) of crude solid. The crude material was adsorbed onto silica gel and chromatographed on silica gel using dichloromethane-hexanes (gradient: 50%-100%). The material from the column was crystallized from ether-hexanes to afford 52 mg (67%) of the title compounds as a white solid, m.p. 189° C.-191° C.; MS: m/z 409.15 (M−).

후처리

  1. temperaturethe mixture was cooled
  2. extractionextracted with three 7 mL portions of ethyl acetate
  3. washThe combined organic layers were washed with three 5 mL portions of 1 N aqueous HCl, 5 mL of brine, three 5 mL portions of saturated aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford 62 mg (82.1%) of crude solid
  8. customchromatographed on silica gel
  9. customThe material from the column was crystallized from ether-hexanes

출처 및 근거

ORD 기록
ord-251cb68304314dcc9226e5c3d1bbce9f
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741361B2

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