Sodium Carbonate → HCID 59015809, compound

HRID 968551Notes

Reaction equation

HRID 968551 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][C:11]1[C:16]([CH3:17])=[CH:15][N:14]=[C:13](Cl)[CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC=CC=1.C(OCC)(=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>[NH2:10][C:11]1[C:16]([CH3:17])=[CH:15][N:14]=[C:13]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:12]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 126437062-Chloro-5-methylpyridin-4-amine

Product 1

HCID 59015809HCID 59015809, compoundYield 62.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phenylboronic acid (188 mg, 1.5 mmol, 1.1 equiv.) and 11 (200 mg, 1.4 mmol, 1.0 equiv.) were dissolved in benzene (5 mL). Aqueous Na2CO3 (1 mL) was then added, followed by Pd(PPh3)4 (324 mg, 0.28 mmol, 0.2 equiv.). The resulting mixture was refluxed for 16 hours. The reaction mixture was dissolved in ethyl acetate and washed with water. The organic extract was dried over Na2SO4 and the solvent evaporated. The crude material was purified by reverse phase HPLC (Acetonitrile/water/TFA), to give 12 as a colorless solid (160 mg, 0.87 mmol, HPLC Rt=3.373 minutes; FIA ES+ 185.1, ES− not observed).

Workup

  1. temperatureThe resulting mixture was refluxed for 16 hours
  2. washwashed with water
  3. extractionThe organic extract
  4. dry with materialwas dried over Na2SO4
  5. customthe solvent evaporated
  6. customThe crude material was purified by reverse phase HPLC (Acetonitrile/water/TFA)

Sources & evidence

ORD record
ord-abb7d8d2fd01460aa2a2c1ccfacfb91d
Source dataset
uspto-grants-2007_12
Patent number
US07304061B2

Reaction notes

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