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

HRID 2369643ノート

反応式

HRID 2369643 の反応式
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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ff0765d7a8ad4841bae77383467d0fe9
出典データセット
uspto-grants-2014_04
特許番号
US08703978B2

反応ノート

読み込み中…