Benzo(b)thiophene, 3-bromo- → N-(1-Benzo[b]thiophen-3-ylmethyl-2,2,2-trifluoroethyl)-2,4,6-trimethylbenzenesulfonamide

HRID 1868424

반응식

HRID 1868424 반응식
[Mg].Br[C:3]1[C:4]2[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=2[S:6][CH:7]=1.[F:12][C:13]([F:30])([F:29])[CH:14]1[CH2:16][N:15]1[S:17]([C:20]1[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=1[CH3:28])(=[O:19])=[O:18]>C1COCC1.[Cu]I>[S:6]1[CH:7]=[C:3]([CH2:16][CH:14]([NH:15][S:17]([C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=2[CH3:28])(=[O:19])=[O:18])[C:13]([F:29])([F:12])[F:30])[C:4]2[CH:11]=[CH:10][CH:9]=[CH:8][C:5]1=2

참가 물질

6

반응물 3

HCID 123250Benzo(b)thiophene, 3-bromo-HCID 5462224MagnesiumHCID 574740362-Trifluoromethyl-1-(2,4,6-trimethylbenzenesulfonyl)aziridine

생성물 1

HCID 11575514N-(1-Benzo[b]thiophen-3-ylmethyl-2,2,2-trifluoroethyl)-2,4,6-trimethylbenzenesulfonamide수율 23.4%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

A mixture of 9 mg (2.20 mmol) of magnesium powder, 79 mg (0.37 mmol) of 3-bromobenzo[b]thiophene, 8 mg (0.04 mmol) of copper (I) iodide, and 50 mg (0.17 mmol) of 2-trifluoromethyl-1-(2,4,6-trimethylbenzenesulfonyl)aziridine in 1 mL of THF was warmed at 80° C. in a sealed tube. After 30 minutes, the reaction was quenched with 7 mL of saturated aqueous ammonium chloride solution and extracted with three 7 mL portions of ethyl acetate. The combined organic layers were washed with two 5 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was chromatographed on silica gel using dichloromethane-hexanes (1:1) to load the sample and then eluting with dichloromethane-hexanes (1:1, then 75:25). The material from the column was triturated with ether-hexanes to afford 17 mg (23%) of the title compound as a white solid which is consistent with the desired product. MS: m/z 428.51 (M+1).

후처리

  1. customthe reaction was quenched with 7 mL of saturated aqueous ammonium chloride solution
  2. extractionextracted with three 7 mL portions of ethyl acetate
  3. washThe combined organic layers were washed with two 5 mL portions of brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was chromatographed on silica gel
  8. washeluting with dichloromethane-hexanes (1:1
  9. customThe material from the column was triturated with ether-hexanes

출처 및 근거

ORD 기록
ord-ca8804da21c84c98af4f2a782c9c84b0
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07635711B2

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