Ethanol → Methyl 6-(4'-pentylbiphenyl-4-yl)-2-phenyl-2-(4-pyrrolidinophenyl)-2h-naphtho[1,2-b]pyran-5-carboxylate

HRID 2369643노트

반응식

HRID 2369643 반응식
FC(F)(F)S(O[C:7]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:10]2OC[C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[CH:14]=[C:9]2[C:8]=1C(OC)=O)(=O)=O.[CH2:44]([C:49]1[CH:54]=[CH:53][C:52]([C:55]2[CH:60]=[CH:59][C:58](B(O)O)=[CH:57][CH:56]=2)=[CH:51][CH:50]=1)[CH2:45][CH2:46][CH2:47][CH3:48].[C:64]([O-])([O-])=[O:65].[K+].[K+].[OH2:70].[CH3:71][CH2:72][OH:73]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:44]([C:49]1[CH:54]=[CH:53][C:52]([C:55]2[CH:60]=[CH:59][C:58]([C:10]3[C:32]4[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:7]4[O:70][C:13]([C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=5)([C:15]5[CH:16]=[CH:17][C:18]([N:21]6[CH2:25][CH2:24][CH2:23][CH2:22]6)=[CH:19][CH:20]=5)[CH:14]=[CH:9][C:8]=4[C:71]=3[C:72]([O:65][CH3:64])=[O:73])=[CH:57][CH:56]=2)=[CH:51][CH:50]=1)[CH2:45][CH2:46][CH2:47][CH3:48]

참가 물질

8

반응물 5

HCID 702EthanolHCID 962WaterHCID 11430Potassium CarbonateHCID 154580894'-Pentyl-4-biphenylboronic Acid (contains varying amounts of Anhydride)HCID 866536106-trifluoromethanesulfonyloxy-5-methoxycarbonyl-3-phenyl-3-(4-pyrrolidinophenyl)-2H-naphtho[1,2-b]pyran

생성물 1

HCID 58274176Methyl 6-(4'-pentylbiphenyl-4-yl)-2-phenyl-2-(4-pyrrolidinophenyl)-2h-naphtho[1,2-b]pyran-5-carboxylate수율 32%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

A mixture of 6-trifluoromethanesulfonyloxy-5-methoxycarbonyl-3-phenyl-3-(4-pyrrolidinophenyl)-2H-naphtho[1,2-b]pyran (0.96 g, 1.6 mmol), 4′-pentyl-4-biphenylboronic acid (0.66 g, 2.5 mmol), K2CO3 (0.68 g, 49 mmol) and Pd(PPh3)4 (91 mg, 3 mol %) in PhMe (30 mL) and EtOH (30 mL) was heated at reflux for 2 h. The resulting solution was cooled, poured into water (100 mL), extracted with DCM (4×50 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was chromatographed twice on silica using PhMe (80% in hexanes). The solvent was removed under reduced pressure and the residue crystallized from acetone-MeOH to give the title compound (0.36 g, 32%) as a purple powder.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperatureThe resulting solution was cooled
  4. extractionextracted with DCM (4×50 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure
  7. customThe residue was chromatographed twice on silica
  8. customThe solvent was removed under reduced pressure
  9. customthe residue crystallized from acetone-MeOH

출처 및 근거

ORD 기록
ord-ff0765d7a8ad4841bae77383467d0fe9
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703978B2

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