Sodium Carbonate → HCID 11692407, compound

HRID 732803Notes

Reaction equation

HRID 732803 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13](=[O:29])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:16][CH:15]=1)=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=[CH:6]2.[CH3:38][S:39]([C:42]1[CH:47]=[CH:46][C:45](B(O)O)=[CH:44][CH:43]=1)(=[O:41])=[O:40].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:38][S:39]([C:42]1[CH:47]=[CH:46][C:45]([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:9]=2[C:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:16][CH:15]=2)=[O:29])=[CH:44][CH:43]=1)(=[O:41])=[O:40]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776Triphenylphosphine2×HCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 11685250Trifluoromethanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)benzoyl]-naphthalen-2-yl ester

Product 1

HCID 11692407HCID 11692407, compoundYield 104.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst2×HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Dissolve trifluoro-methanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-yl ester (555 mg, 1.0 mmol), 4-methansulfonylphenylboronic acid (310 mg, 1.55 mmol), Pd(OAc)2 (23.9 mg, 0.11 mmol), Ph3P (54.2 mg, 0.21 mmol) and Na2CO3 (2.5 mL, 2M in water) in ethyleneglycol dimethyl ether (DME, 30 mL). Reflux the mixture for 2 hours and add additional Pd(OAc)2 (25.2 mg) and Ph3P (58.9 mg). Reflux for 2 hours then dilute the reaction mixture with water and extract with chloroform. Dry the organic phase over Na2SO4, filter and concentrate. Purify the crude material by loading on an SCX column and eluting with 2M NH3/MeOH to afford 569 mg of the title compound (101%). LCMS: m/z=544 (M+H)+

Workup

  1. temperatureReflux the mixture for 2 hours
  2. temperatureReflux for 2 hours
  3. extractionextract with chloroform
  4. dry with materialDry the organic phase over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the crude material by loading on an SCX column
  8. washeluting with 2M NH3/MeOH

Sources & evidence

ORD record
ord-ca42a2a1e27c428aa67202a28270fe2a
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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