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

HRID 2196536노트

반응식

HRID 2196536 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
75 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-dfa2442293dc4e2f9630f3b96f06f6cf
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338437B2

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