Acetonitrile → 6-(5-Fluoro-2-methylphenyl)-1-(3-fluoro-2-nitrophenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol

HRID 400663노트

반응식

HRID 400663 반응식
[F:1][C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4](OS(C(F)(F)F)(=O)=O)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.C(#N)C.[F:29][C:30]1[CH:31]=[CH:32][C:33]([CH3:49])=[C:34]([C:36]([CH3:48])([CH3:47])[CH2:37][C:38]([C:43]([F:46])([F:45])[F:44])([OH:42])[CH2:39][C:40]#[CH:41])[CH:35]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.O1CCCC1>[F:29][C:30]1[CH:31]=[CH:32][C:33]([CH3:49])=[C:34]([C:36]([CH3:47])([CH3:48])[CH2:37][C:38]([C:43]([F:44])([F:45])[F:46])([OH:42])[CH2:39][C:40]#[C:41][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=2[N+:16]([O-:18])=[O:17])[CH:35]=1

참가 물질

9

반응물 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 469390162-(1,1-Dimethyl-3-hydroxy-3-trifluoromethyl-5-hexynyl)-4-fluorotolueneHCID 600266203-Fluoro-2-nitrophenyl trifluoromethanesulphonate

생성물 1

HCID 600264926-(5-Fluoro-2-methylphenyl)-1-(3-fluoro-2-nitrophenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol수율 45.3%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 67553Tetrabutylammonium Iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of trifluoromethanesulfonic acid 3-fluoro-2-nitrophenyl ester (149 mg, 0.52 mmol), dichlorobis(triphenylphosphine)palladium (II) (20 mg, 0.028 mmol), copper (I) iodide (14 mg, 0.074 mmol), tetrabutyl ammonium iodide (200 mg, 0.54 mmol), 0.25 mL of anhydrous triethylamine, 0.5 mL of anhydrous acetonitrile, and 0.5 mL of anhydrous tetrahydrofuran was stirred at room temperature for 30 minutes. The resulting mixture was treated with 6-(5-fluoro-2-methylphenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol (145 mg, 0.48 mmol) and stirred at room temperature for 18 hours. The crude product was purified by chromatography on SiO2 (50% hexanes in dichloromethane) to give 96 mg of the title product as light yellow oil, (45% yield).

후처리

  1. stirringstirred at room temperature for 18 hours
  2. customThe crude product was purified by chromatography on SiO2 (50% hexanes in dichloromethane)

출처 및 근거

ORD 기록
ord-e66f46184a51474db2757ffd1848176d
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741897B2

반응 노트

불러오는 중…