Sodium Carbonate → HCID 69255012, compound

HRID 2217155Notes

Reaction equation

HRID 2217155 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1B(O)O.[CH3:20][O:21][C:22]1[C:23]([O:54][CH3:55])=[CH:24][C:25]2[N:31]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:30](=O)[C@@H:29]3[CH2:41][C:42](OS(C(F)(F)F)(=O)=O)=[CH:43][N:28]3[C:27](=[O:52])[C:26]=2[CH:53]=1>C(O)C.O.C1C=CC=CC=1.C(OCC)(=O)C.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>[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[C:42]1[CH2:41][CH:29]2[N:28]([CH:43]=1)[C:27](=[O:52])[C:26]1[CH:53]=[C:22]([O:21][CH3:20])[C:23]([O:54][CH3:55])=[CH:24][C:25]=1[N:31]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:38])([CH3:37])[CH3:39])[CH2:30]2

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734375(Naphthalen-2-yl)boronic acidHCID 59767717HCID 59767717, compound

Product 1

HCID 69255012HCID 69255012, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 66847609Benzene ethanol waterSolvent

Procedure

Sodium carbonate (300 mg, 2.83 mmol), 2-napthaleneboronic acid (171 mg, 0.99 mmol) and tetrakis(triphenylphosphine)palladium(0) (30 mg) were added to a solution of 9 (517 mg, 0.93 mmol) in ethanol/water/benzene (20/20/20 mL) and stirred at room temperature for 96 hours. The reaction mixture was diluted with ethyl acetate (220 mL) and washed with water (50 mL) and brine (50 mL) and dried over magnesium sulphate. The crude product was purified by flash column chromatography using 70% ethyl acetate in hexane as eluent to give the pure product 10 as a yellow oil.

Workup

  1. washwashed with water (50 mL) and brine (50 mL)
  2. dry with materialdried over magnesium sulphate
  3. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-6db789aa85d047878bc86581c1364b4d
Source dataset
uspto-grants-2008_08
Patent number
US07407951B2

Reaction notes

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