Nitrogen → HCID 59784760, compound

HRID 470331Notes

Reaction equation

HRID 470331 reaction equation
NC1C(C(O)=O)=CN(C2N=CC3CC[C:14]4[CH:20]=[C:21]([O:24][CH3:25])C=C[C:13]=4[C:12]=3[N:11]=2)N=1.Br[C:27]1[CH:39]=[CH:38][C:30]2[NH:31]C(C(Cl)(Cl)Cl)=[N:33][C:29]=2[CH:28]=1.C([O-])([O-])=O.[Na+].[Na+].N#N>O1CCOCC1.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>[NH2:33][C:29]1[CH:28]=[C:27]([C:20]2[C:21]([O:24][CH3:25])=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:39]=[CH:38][C:30]=1[NH2:31]

Participants

7

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 59784811HCID 59784811, compoundHCID 178478477HCID 178478477, compound

Product 1

HCID 59784760HCID 59784760, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-bromo-o-phenylenediamine 1 (0.935 g, 5 mmol), 2-methoxy-3-pyridyl boronic acid 2 and Na2CO3 (1.060 g, 10 mmols) in 1,4-dioxane/H2O (3:1, 20 mL) flushed with N2 was added Pd(PPh3)4 (0.575 g, 0.5 mmol) in one portion. Resulting reaction mixture was stirred under N2 atmosphere at 100° C. for 12 h. Solvent was evaporated and residue was extracted with ethyl acetate (20 mL). Dried over anhydrous sodiumsulfate. Filtered, and evaporation of solvent gave a crude residue which was used as such in the following reaction. (0.850 g).

Workup

  1. customResulting
  2. customreaction mixture
  3. customSolvent was evaporated
  4. extractionresidue was extracted with ethyl acetate (20 mL)
  5. dry with materialDried over anhydrous sodiumsulfate
  6. filtrationFiltered
  7. customevaporation of solvent

Sources & evidence

ORD record
ord-926afb42ee6645948b223723205ca28a
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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