Sodium Carbonate → HCID 54747868, compound

HRID 2094768Notes

Reaction equation

HRID 2094768 reaction equation
Br[C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])=[C:10]([OH:21])[C:9]3[CH2:22][S:23][CH2:24][C:8]2=3)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:33]1([CH3:42])[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1>CC(N(C)C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:21][C:10]1[C:9]2[CH2:22][S:23][CH2:24][C:8]=2[N:7]([CH2:6][C:5]2[CH:25]=[CH:26][C:2]([C:36]3[CH:37]=[CH:38][C:33]([CH3:42])=[CH:34][CH:35]=3)=[CH:3][CH:4]=2)[C:12](=[O:13])[C:11]=1[C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 54747824HCID 54747824, compound

Product 1

HCID 54747868HCID 54747868, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
115 °C

Procedure

The product of Example 2 (2-1) (0.08 g, 0.16 mmol) was dissolved in DMA (2 mL) in a 10 mL reaction tube of a CEM Corporation Discover 300 Watt microwave reactor. An aq solution of Na2CO3 (2 M, 0.8 mL, 1.6 mmol), 4-tolylboronic acid (40 mg, 0.29 mmol) and bis(triphenylphosphine)palladium(II) chloride (11 mg, 0.016 mmol) were added and the tube was purged with nitrogen, capped and inserted into the microwave reactor. It was heated at 115° C., 50 watts maximum power, for 15 min. The reaction was diluted with EtOAc, washed with 2 M HCl, dried (Na2SO4), filtered and concentrated. The residue was purified by semi-preparative reverse phase HPLC on a C18 column eluted with 0-100% MeCN in water. The desired fractions were concentrated, dissolved in EtOAc and washed with water. The organic layer was dried (Na2SO4), filtered and concentrated affording the title compound (25-1). 450.9 (M+1); Rt=3.52 min.

Workup

  1. customthe tube was purged with nitrogen
  2. customcapped
  3. additionThe reaction was diluted with EtOAc
  4. washwashed with 2 M HCl
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by semi-preparative reverse phase HPLC on a C18 column
  9. washeluted with 0-100% MeCN in water
  10. concentrationThe desired fractions were concentrated
  11. dissolutiondissolved in EtOAc
  12. washwashed with water
  13. dry with materialThe organic layer was dried (Na2SO4)
  14. filtrationfiltered
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-bef1c1bbad1142f78c9e776663448e12
Source dataset
uspto-grants-2013_05
Patent number
US08445680B2

Reaction notes

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