Potassium Carbonate → HCID 59627866, compound

HRID 1256675Notes

Reaction equation

HRID 1256675 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:11])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>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.C1COCC1>[NH2:11][C:4]1[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=[C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 589057095-Bromo-2-nitropyridin-3-amine

Product 1

HCID 59627866HCID 59627866, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

To 5-bromo-3-amino-2-nitropyridine (190 mg, 0.872 mmol) in a dry microwave reaction tube were added phenylboronic acid (159 mg, 1.31), K2CO3 (361 mg, 2.61 mmol) and Pd(PPh3)4 (101 mg, 0.087 mmol) and the reaction flask was evacuated and flushed with N2 four times. To this solid reaction mixture was added anhydrous THF (2 mL) and the reaction mixture was degassed by applying vacuum and flushing with N2 five times and sealed in N2 atmosphere. The reaction mixture was then heated 120° C. for 2 h. After this time, LC/MS analysis of the reaction mixture should essentially show the desired product. Reaction mixture was concentrated in vacuo and to the residue was added MeOH and stirred for 30 min. All the solids were collected by filtration and washed thoroughly with MeOH and water MS: cal'd 216 (M+H)+, exp 216 (M+H)+

Workup

  1. customthe reaction flask was evacuated
  2. customflushed with N2 four times
  3. customTo this solid reaction mixture
  4. customthe reaction mixture was degassed
  5. customflushing with N2 five times
  6. customsealed in N2 atmosphere
  7. customReaction mixture
  8. concentrationwas concentrated in vacuo and to the residue
  9. additionwas added MeOH
  10. filtrationAll the solids were collected by filtration
  11. washwashed thoroughly with MeOH and water MS

Sources & evidence

ORD record
ord-98c9d1936eda409ca512e6e73010a660
Source dataset
uspto-grants-2013_06
Patent number
US08461189B2

Reaction notes

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