Sodium Carbonate → HCID 66652141, compound

HRID 418927Notes

Reaction equation

HRID 418927 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH:8]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH:9]3[CH2:15][CH2:14][CH2:13][CH:10]32)=[C:5](OS(C(F)(F)F)(=O)=O)[CH:4]=1.[Cl:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.C1(C)C=CC=CC=1.C(O)C>[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:12]=[C:11]3[C:6]=2[CH2:7][CH:8]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[CH:9]2[CH2:15][CH2:14][CH2:13][CH:10]23)=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 72309420HCID 72309420, compound

Product 1

HCID 66652141HCID 66652141, compoundYield 310.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
90 °C

Procedure

Combine trifluoro-methanesulfonic acid 8-methoxy-4-(4-methoxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalen-6-yl ester (0.046 g, 0.1 mmol), 4-chlorophenyboronic acid (0.019 g, 0.12 mmol), tetrakis(triphenylphosphine)palladium(0) (0.006 g, 5 mole %), sodium carbonate (0.12 ml 2N), and toluene/ethanol (4-1). Purge in vacuo briefly, and heat at 90° C. for 12 hours. Remove solvent, take in ethyl acetate and wash with water. Dry over anhydrous sodium sulfate and chromatograph the residue on silica gel with 5% ethyl acetate in hexanes to yield the titled compound (0.13 g, 31%). 1H NMR (CDCl3): 7.34 (d, J=8.8 Hz, 2H), 7.26 (d, J=8.8 Hz, 2 H), 7.1 (d, J=8.87 Hz, 2H), 6.8 (d, J=8.8 Hz, 2H), 6.78 (s, 1H), 6.62 (s, 1H), 3.82 (s, 3H), 3.77 (s, 3H), 3.45 (m, 1H), 2.98 (m, 1H), 2.85(m, 1H), 2.57 (m, 1H), 2.3 (m, 1H), 2.21 (m, 1H), 1.65-1.2 (m, 5H).

Workup

  1. customPurge in vacuo briefly
  2. washwash with water
  3. dry with materialDry over anhydrous sodium sulfate and chromatograph the residue on silica gel with 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-9dcc7baf3bfc4c97abc33b144095780b
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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