Heptane → 2-[4-(3-Methanesulfonyl-phenyl)-imidazol-1-yl]-4-trifluoromethyl-6-(4-trifluoromethylphenyl)-pyrimidine

HRID 1989520노트

반응식

HRID 1989520 반응식
C([Sn](CCCC)(CCCC)[C:6]1[N:7]=[CH:8][N:9]([C:11]2[N:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)[N:12]=2)[CH:10]=1)CCC.BrC1C=C([CH2:46][S:47](CC2C=CC=C(Br)C=2)(=[O:49])=[O:48])C=CC=1.C[CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64]>C1(C)C=CC=CC=1>[CH3:46][S:47]([C:64]1[CH:63]=[C:62]([C:6]2[N:7]=[CH:8][N:9]([C:11]3[N:16]=[C:15]([C:17]([F:18])([F:19])[F:20])[CH:14]=[C:13]([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:30])[F:29])=[CH:23][CH:22]=4)[N:12]=3)[CH:10]=2)[CH:61]=[CH:60][CH:59]=1)(=[O:49])=[O:48]

참가 물질

5

반응물 3

HCID 8900HeptaneHCID 534433923-Bromophenylmethyl sulphoneHCID 574688252-(4-Tributylstannanyl-imidazol-1-yl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidine

생성물 1

HCID 574689892-[4-(3-Methanesulfonyl-phenyl)-imidazol-1-yl]-4-trifluoromethyl-6-(4-trifluoromethylphenyl)-pyrimidine수율 64%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A stirred mixture of 2-(4-tributylstannanyl-imidazol-1-yl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidine (Example G.1) (0.155 g, 0.24 mmol), commercially available 3-bromo-phenylmethyl sulfone (0.062 g, 0.26 mmol), tetrakis(triphenyl-phosphine)palladium (0.017 g, 0.015 mmol) in toluene (5 mL) was heated under reflux conditions for 15 h. Heptane (5 mL) was added at room temperature and the mixture was stirred for 1 h. The precipitate was collected by filtration, washed with heptane and dried. Further purification by flash chromatography on silica gel (ethyl acetate/heptane) and crystallization (dichloromethane/hexane) yielded the title compound (0.078 g, 64%) as a white solid. MS (ISP) 512.9 [(M+H)+]; mp 231° C.

후처리

  1. temperaturewas heated under reflux conditions for 15 h
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with heptane
  4. customdried
  5. customFurther purification by flash chromatography
  6. customon silica gel (ethyl acetate/heptane) and crystallization (dichloromethane/hexane)

출처 및 근거

ORD 기록
ord-28d9c515180f44729f5fff9a1505efec
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07642264B2

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