Potassium Carbonate → benzyl 4-(3-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate

HRID 2196536ノート

反応式

HRID 2196536 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13](B3OC(C)(C)C(C)(C)O3)[CH:12]=2)[N:9]=[C:8]([C:26]([F:29])([F:28])[F:27])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[C:42]1[CH2:47][CH2:46][N:45]([C:48]([O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[O:49])[CH2:44][CH:43]=1)(=O)=O>CN(C=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:12]=[C:13]([C:42]3[CH2:47][CH2:46][N:45]([C:48]([O:50][CH2:51][C:52]4[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=4)=[O:49])[CH2:44][CH:43]=3)[CH:14]=[CH:15][CH:16]=2)[N:9]=[C:8]([C:26]([F:29])([F:28])[F:27])[CH:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 11303044benzyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylateHCID 598433125-(furan-2-yl)-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(trifluoromethyl)-1H-pyrazole

生成物 1

HCID 59843270benzyl 4-(3-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate収率 66.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

To a stirred solution of 63 (533 mg, 1.319 mmol) in DMF (6.6 mL) were added potassium carbonate (419 mg, 3.03 mmol) and benzyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1 (2H)-carboxylate (578 mg, 1.582 mmol) followed by 1,1′-bis(diphenylphosphino)ferrocenedichloro palladium(II) dichloromethane complex (58 mg, 0.079 mmol). The resulting suspension was allowed to stir at 75° C. for 4 h. The mixture then was filtered through celite and washed with EtOAc. The organic phase was washed with brine and dried over Na2SO4. The solution was then evaporated to dryness. The residue was purified via silica gel flash chromatography (5% to 40% EtOAc/hexanes). The title product 64 (430 mg, 66% yield) was isolated as a colorless oil. LRMS (ESI): calc. 493.5; found 494.5 (MH)+.

後処理

  1. filtrationThe mixture then was filtered through celite
  2. washwashed with EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solution was then evaporated to dryness
  6. customThe residue was purified via silica gel flash chromatography (5% to 40% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-dfa2442293dc4e2f9630f3b96f06f6cf
出典データセット
uspto-grants-2012_12
特許番号
US08338437B2

反応ノート

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