Water → HCID 56723596, compound

HRID 1918387Notes

Reaction equation

HRID 1918387 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Br[C:14]1[CH:15]=[N:16][CH:17]=[C:18]([CH:23]=1)[C:19]([O:21][CH3:22])=[O:20].C([O-])([O-])=O.[Cs+].[Cs+].O>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>[CH3:22][O:21][C:19](=[O:20])[C:18]1[CH:23]=[C:14]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=2)[CH:15]=[N:16][CH:17]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 10796Cesium carbonateHCID 699336Methyl 5-bromopyridine-3-carboxylateHCID 32475223-Chloro-4-methoxybenzeneboronic acid

Product 1

HCID 56723596HCID 56723596, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

6.5 g of 3-chloro-4-methoxyphenylboronic acid, 5.0 g of methyl 5-bromonicotinate, 1.3 g of tetrakis(triphenylphosphine)palladium(0), and 22.6 g of Cs2CO3 were stirred in 325 ml of DMF and 65 ml of water for 3 h at 45° C. The reaction mixture was then poured into 750 ml of water and extracted three times using 300 ml of EA each. The combined organic layers were then washed twice using 150 ml of water each. The organic layer was then dried using MgSO4 and evaporated. Chromatography on silica gel using EA/HEP (gradient) yielded 2.4 g of the title compound, colorless oil.

Workup

  1. extractionextracted three times
  2. washThe combined organic layers were then washed twice
  3. customThe organic layer was then dried
  4. customevaporated

Sources & evidence

ORD record
ord-a9d1e7035aa94b6194e945c6302d3644
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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