Sodium Carbonate → HCID 67155496, compound

HRID 389668Notes

Reaction equation

HRID 389668 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Br[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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>[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 122863-BromopyridineHCID 541578433-Bromo-2-methylphenylboronic acid

Product 1

HCID 67155496HCID 67155496, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

(3-Bromo-2-methylphenyl)boronic acid (3 g, 13.96 mmol) and 3-bromopyridine (2.69 ml, 27.92 mmol) in toluene (24 ml) were stirred under argon, then Na2CO3 (5.18 g, 48.86 mmol) and Pd(PPh3)4 (161 mg, 0.14 mmol) were added and the reaction was heated to 110° C. for 48 h. The solvent was evaporated and after addition of ethyl acetate the organic layer was filtered through Celite, then washed with water and dried with Na2SO4, evaporated to dryness and the product was obtained and used without further purification in step 22.2. Yield: 3.01 g, 87

Workup

  1. customThe solvent was evaporated
  2. additionafter addition of ethyl acetate the organic layer
  3. filtrationwas filtered through Celite
  4. washwashed with water
  5. dry with materialdried with Na2SO4
  6. customevaporated to dryness
  7. customthe product was obtained
  8. customused without further purification in step 22.2

Sources & evidence

ORD record
ord-6d6e400712974ef28a447842e69a79b6
Source dataset
uspto-grants-2013_02
Patent number
US08378092B2

Reaction notes

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