Toluene → Methyl 2-(4-diethylaminophenyl)-2-phenyl-6-(4'-pentylbiphenyl-4-yl)-2H-naphtho[1,2-b]pyran-5-carboxylate

HRID 2369644Notes

Reaction equation

HRID 2369644 reaction equation
[CH2:1]([N:3]([CH2:42][CH3:43])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:36]3C=CC=C[CH:37]=3)[O:15][C:14]3[C:16]4[C:21]([C:22](OS(C(F)(F)F)(=O)=O)=[C:23]([C:24]([O:26][CH3:27])=[O:25])[C:13]=3[CH:12]=[CH:11]2)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:6][CH:5]=1)[CH3:2].[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([O-])([O-])=O.[K+].[K+].[C:70]1(C)[CH:75]=CC=[CH:72][CH:71]=1>C(O)C>[CH2:1]([N:3]([CH2:42][CH3:43])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:36]3[CH:37]=[CH:72][CH:71]=[CH:70][CH:75]=3)[O:15][C:14]3[C:16]4[C:21]([C:22]([C:58]5[CH:59]=[CH:60][C:55]([C:52]6[CH:53]=[CH:54][C:49]([CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])=[CH:50][CH:51]=6)=[CH:56][CH:57]=5)=[C:23]([C:24]([O:26][CH3:27])=[O:25])[C:13]=3[CH:12]=[CH:11]2)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 154580894'-Pentyl-4-biphenylboronic Acid (contains varying amounts of Anhydride)HCID 58274187Methyl 2-(4-diethylaminophenyl)-2-phenyl-6-trifluoromethanesulfonyloxy-2H-naphtho[1,2-b]pyran-5-carboxylate

Product 1

HCID 58274171Methyl 2-(4-diethylaminophenyl)-2-phenyl-6-(4'-pentylbiphenyl-4-yl)-2H-naphtho[1,2-b]pyran-5-carboxylateYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution containing methyl 2-(4-diethylamino-phenyl)-2-phenyl-6-trifluoromethanesulfonyloxy-2H-naphtho[1,2-b]pyran-5-carboxylate (0.90 g, 1.47 mmol), 4′-pentyl-4-biphenylboronic acid (0.39 g. 1.47 mmol), K2CO3 (0.30 g), PhMe (30 mL), ethanol (30 mL) and degassed for 1 h. Pd(PPh3)4 (0.085 g, 5% mol) was added and the reaction mixture was heated at reflux for 16 hrs. The reaction mixture was poured into water (100 mL), extracted with DCM (4×50 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was chromatographed on silica using DCM (20% hexanes) and recrystallised from acetone-MeOH to give a pale blue powder (2.3 g, 30%) mp: 177-178° C.

Workup

  1. customdegassed for 1 h
  2. additionPd(PPh3)4 (0.085 g, 5% mol) was added
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 16 hrs
  5. additionThe reaction mixture was poured into water (100 mL)
  6. extractionextracted with DCM (4×50 mL)
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed under reduced pressure
  9. customThe residue was chromatographed on silica
  10. customrecrystallised from acetone-MeOH

Sources & evidence

ORD record
ord-7a65df1a0db545e0b4a39152b6696754
Source dataset
uspto-grants-2014_04
Patent number
US08703978B2

Reaction notes

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