Sodium Carbonate → HCID 86688545, compound

HRID 710548Notes

Reaction equation

HRID 710548 reaction equation
Br[C:2]1[CH:26]=[CH:25][C:5]2[N:6]=[C:7]([NH:9][C:10]([N:12]3[CH2:17][CH2:16][C:15](=[CH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[CH2:14][CH2:13]3)=[O:11])[S:8][C:4]=2[CH:3]=1.CC1(C)C(C)(C)OB([C:35]2[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>C(COC)OC.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>[N:37]1[CH:38]=[CH:39][CH:40]=[C:35]([C:2]2[CH:26]=[CH:25][C:5]3[N:6]=[C:7]([NH:9][C:10]([N:12]4[CH2:17][CH2:16][C:15](=[CH:18][C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=5)[CH2:14][CH2:13]4)=[O:11])[S:8][C:4]=3[CH:3]=2)[CH:36]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 27346563-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 86688544HCID 86688544, compound

Product 1

HCID 86688545HCID 86688545, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

The compound (50 mg, 116 μmol) obtained in Example 1 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (119 mg, 580 μmol) were dissolved in dimethoxyethane (3 mL), under a nitrogen atmosphere, a 2N sodium carbonate aqueous solution (350 μL, 700 μmol) and tetrakis(triphenylphosphine)palladium(0) (26.8 mg, 23.2 μmol) were added thereto, followed by stirring for 16 hours while heating under reflux. A saturated ammonium chloride aqueous solution was added to the resulting mixture to stop the reaction, and after extraction with ethyl acetate, the extract was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The desiccant was filtered off, and the residue obtained by evaporation under reduced pressure was purified using medium pressure flash column chromatography (silica gel; methanol:chloroform=1:25), thereby giving the title compound (26.3 mg, 53%) as an amorphous solid.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. customthe reaction
  4. extractionafter extraction with ethyl acetate
  5. washthe extract was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe desiccant was filtered off
  8. customthe residue obtained by evaporation under reduced pressure
  9. customwas purified

Sources & evidence

ORD record
ord-6dd94c33144c452696c8b216ece0b0bf
Source dataset
uspto-grants-2015_11
Patent number
US09181183B2

Reaction notes

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