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 1989761노트

반응식

HRID 1989761 반응식
[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]

참가 물질

4

반응물 2

HCID 57468693Trifluoro-methanesulfonic acid 6-methyl-4-(4-trifluoromethoxyphenyl)-pyridin-2-yl esterHCID 60209340HCID 60209340, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ef81cb4ea2d640e0ae36301d3183faf7
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07642264B2

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