Trifluoro-methanesulfonic acid 6-methyl-4-(4-trifluoromethoxyphenyl)-pyridin-2-yl ester → N-tert-Butyl-3-[6'-methyl-4'-(4-trifluoromethoxy-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonamide

HRID 1989761ノート

反応式

HRID 1989761 の反応式
[CH3:1][C:2]1[N:7]=[C:6](OS(C(F)(F)F)(=O)=O)[CH:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=2)[CH:3]=1.[C:27]([NH:31][S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]2[CH:46]=[CH:45][CH:44]=[C:43]([Sn](CCCC)(CCCC)CCCC)[N:42]=2)[CH:36]=1)(=[O:34])=[O:33])([CH3:30])([CH3:29])[CH3:28]>C1(C)C=CC=CC=1>[C:27]([NH:31][S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]2[N:42]=[C:43]([C:6]3[CH:5]=[C:4]([C:16]4[CH:17]=[CH:18][C:19]([O:22][C:23]([F:24])([F:25])[F:26])=[CH:20][CH:21]=4)[CH:3]=[C:2]([CH3:1])[N:7]=3)[CH:44]=[CH:45][CH:46]=2)[CH:36]=1)(=[O:33])=[O:34])([CH3:30])([CH3:28])[CH3:29]

参加物

4

反応物 2

HCID 57468693Trifluoro-methanesulfonic acid 6-methyl-4-(4-trifluoromethoxyphenyl)-pyridin-2-yl esterHCID 60209340HCID 60209340、化合物

生成物 1

HCID 24760219N-tert-Butyl-3-[6'-methyl-4'-(4-trifluoromethoxy-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonamide

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A stirred mixture of trifluoro-methanesulfonic acid 6-methyl-4-(4-trifluoromethoxyphenyl)-pyridin-2-yl ester (Example A.63) (0.221 g, 0.55 mmol), N-tert-butyl-3-(6-tributylstannanyl-pyridin-2-yl)-benzenesulfonamide (Example F.6) (0.290 g, 0.50 mmol), tetrakis(triphenyl-phosphine)palladium (0.032 g, 5 mol %) in toluene (5 mL) was heated under reflux conditions for 18 h. Cooled to rt, extracted with ethyl acetate and water, dried the organic layer over Na2SO4. Removal of the solvent in vacuum left a crude product which was purified by silica gel column chromatography with n-heptane/ethyl acetate to give the title compound after trituration with diethyl ether as a white solid (100 mg, 34%). MS (ISP) 542.8 [(M+H)+]; mp 148° C.

後処理

  1. temperaturewas heated under reflux conditions for 18 h
  2. extractionextracted with ethyl acetate and water
  3. dry with materialdried the organic layer over Na2SO4
  4. customRemoval of the solvent in vacuum
  5. waitleft a crude product which
  6. customwas purified by silica gel column chromatography with n-heptane/ethyl acetate

出典と根拠

ORDレコード
ord-ef81cb4ea2d640e0ae36301d3183faf7
出典データセット
uspto-grants-2010_01
特許番号
US07642264B2

反応ノート

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