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

HRID 1989520ノート

反応式

HRID 1989520 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-28d9c515180f44729f5fff9a1505efec
出典データセット
uspto-grants-2010_01
特許番号
US07642264B2

反応ノート

読み込み中…