Sodium Carbonate → HCID 22000072, compound

HRID 1975947Notes

Reaction equation

HRID 1975947 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][CH3:9].C(=O)([O-])[O-].[Na+].[Na+].[C:16]1([CH3:25])[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O>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.C1(C)C=CC=CC=1>[CH3:9][NH:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH3:25]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 130982014-Pyridinamine,3-bromo-N-methyl-(9CI)

Product 1

HCID 22000072HCID 22000072, compoundYield 12.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.26 g (6.75 mmol) (3-bromo-pyridin-4-yl)-methyl-amine, 13 ml toluene, 7 ml 2 N sodium carbonate solution, 234 mg (0.203 mmol) tetrakis(triphenylphosphine)palladium(0) and 1.01 g (7.43 mmol) o-tolylboronic acid was heated under argon at 80° C. for 12 h. After cooling to room temperature, the aqueous phase was separated and washed twice with toluene. The combined organic layers were washed with brine, dried (sodium sulfate) and evaporated. The residue was purified by flash chromatography to yield 164 mg (12%) of the title compound as a yellow oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe aqueous phase was separated
  3. washwashed twice with toluene
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (sodium sulfate)
  6. customevaporated
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-9fd4d0ac23ed4665bf601f1c4dbb1fb5
Source dataset
uspto-grants-2001_05
Patent number
US06225316B1

Reaction notes

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