Sodium Carbonate → HCID 21830737, compound

HRID 1600931Notes

Reaction equation

HRID 1600931 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=1)[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12].[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][CH2:30][CH:31]([O:43][Si](C(C)(C)C)(C)C)[CH2:32][O:33][C:34]2[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=2)[CH:24]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.[Cl-].[Na+].O.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.C(O)C.C1(C)C=CC=CC=1>[C:14]1([NH:13][C:11]([C:10]2[CH:9]=[C:8]([C:37]3[CH:36]=[CH:35][C:34]([O:33][CH2:32][CH:31]([OH:43])[CH2:30][CH2:29][C:25]4[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=4)=[CH:39][CH:38]=3)[CH:22]=[CH:21][CH:20]=2)=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

10

Reactant 4

HCID 10340Sodium CarbonateHCID 8536523-bromo-N-phenylbenzamideHCID 2724141Tetrabutylammonium FluorideHCID 21717159HCID 21717159, compound

Product 1

HCID 21830737HCID 21830737, compoundYield 11.8%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
120 °C

Procedure

Prepared according to the method described in Example 33a) from toluene (3 ml), aqueous sodium carbonate (2 M, 0.9 ml), ethanol (1.0 ml), 3-bromo-N-phenylbenzamide (0.48 g), (±)-4-[4-(3-pyridyl)-2-(tert-butyldimethylsilyloxy)butoxy]benzeneboronic acid (0.7 g) and tetrakis(triphenylphosphine)palladium(0) (50 mg) with heating at 120° C. for 5 hours. The residue obtained after work up was purified by column chromatography over silica eluting with ethyl acetate:hexane (1:1) to give a colourless oil which was desilylated by treatment with tetrabutylammonium fluoride (0.7 ml; 1 M in tetrahydrofuran) in tetrahydrofuran at 0° C. After stirring at this temperature for 5 minutes a saturated solution of brine (5 ml) was added and the organic phase separated. The aqueous phase was extracted with ethyl acetate (20 ml). The combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethanol:dichloromethane (1:19) to give the title compound as a colourless solid (0.09 g).

Workup

  1. customPrepared
  2. customThe residue obtained after work
  3. customup was purified by column chromatography over silica eluting with ethyl acetate:hexane (1:1)
  4. customto give a colourless oil which
  5. additionwas added
  6. customthe organic phase separated
  7. extractionThe aqueous phase was extracted with ethyl acetate (20 ml)
  8. washThe combined organic phases were washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by column chromatography over silica eluting with ethanol:dichloromethane (1:19)

Sources & evidence

ORD record
ord-b145db7797f948bf9d93d8b542ee30d9
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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