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

HRID 2369643Notes

Reaction equation

HRID 2369643 reaction equation
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]

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ff0765d7a8ad4841bae77383467d0fe9
Source dataset
uspto-grants-2014_04
Patent number
US08703978B2

Reaction notes

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