Sodium Carbonate → HCID 86688547, compound

HRID 710550Notes

Reaction equation

HRID 710550 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.[N:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>C(COC)OC.CN(C=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>[N:27]1[CH:32]=[CH:31][C:30]([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:29][CH:28]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 2734379(Pyridin-4-yl)boronic acidHCID 86688544HCID 86688544, compound

Product 1

HCID 86688547HCID 86688547, compoundYield 17.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

The compound (200 mg, 466 μmol) obtained in Example 1 and pyridine-4-boronic acid (115 mg, 932 μmol) were dissolved in a mixture of dimethoxyethane (4 mL) and DMF (2 mL), and a 2N sodium carbonate aqueous solution (700 μL, 1.40 mmol) and tetrakis(triphenylphosphine)palladium(0) (80 mg, 70 μmol) were added thereto. The resulting mixture was subjected to reaction at 120° C. for 20 minutes in a microwave reactor. A saturated ammonium chloride aqueous solution was added to the resulting mixture to stop the reaction, and the precipitate was collected by filtration. The residue was purified using medium pressure flash column chromatography (silica gel; methanol:chloroform=1:30), thereby giving the title compound (34 mg, 17%) as an amorphous solid.

Workup

  1. customThe resulting mixture was subjected to reaction at 120° C. for 20 minutes in a microwave reactor
  2. customthe reaction
  3. filtrationthe precipitate was collected by filtration
  4. customThe residue was purified

Sources & evidence

ORD record
ord-86efc619807547e39588934d9b735ddd
Source dataset
uspto-grants-2015_11
Patent number
US09181183B2

Reaction notes

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