Ethanol → HCID 10946430, compound

HRID 2180256Notes

Reaction equation

HRID 2180256 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].[CH:9]([N:12]([CH:21]([CH3:23])[CH3:22])[C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:11])[CH3:10].B(O)O.C(=O)([O-])[O-].[K+].[K+].CCO>C1(C)C=CC=CC=1.O>[NH2:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:19]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:13]([N:12]([CH:9]([CH3:10])[CH3:11])[CH:21]([CH3:22])[CH3:23])=[O:20]

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 260954-Amino-3-bromopyridineHCID 178457678HCID 178457678, compound

Product 1

HCID 10946430HCID 10946430, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

The bromopyridine 1 (1.4 g, 8.1 mmol), boronic acid 2 (2.0 g, 8.9 mmol) and potassium carbonate (2.2 g, 15.9 mmol) were dissolved in 80 mL toluene, 8 ml EtOH and 8 mL H2O. This mixture was evacuated and refilled with nitrogen several times. Then, tetrakistriphenylphosphine palladium (0) (350 mg, 0.30 mmol) was added to the mixture and the mixture was heated to 80° C. overnight. Water (100 mL) was then added to the reaction and the organic layer was partitioned. The aqueous layer was extracted with EtOAc (2×100 mL) and the combined organics were dried with Na2CO3 and concentrated. The crude reaction product was triturated with diethyl ether (25 mL) and filtered. The resulting solid (2.0 g, 83%) was collected and characterized as the biphenyl amine 3. 1H NMR (CDCl3): δ 8.17 (d, 1H), 8.03 (s, 1H), 7.45 (m, 2H), 7.25 (m, 2H), 6.55 (d, 1H), 4.50 (bs, 2H), 3.61 (m, 1H), 3.31 (m, 1H), 1.49 (d, 3H), 1.16 (d, 3H), 1.03 (d, 3H), 0.83 (d, 3H).

Workup

  1. customThis mixture was evacuated
  2. additionrefilled with nitrogen several times
  3. customthe organic layer was partitioned
  4. extractionThe aqueous layer was extracted with EtOAc (2×100 mL)
  5. dry with materialthe combined organics were dried with Na2CO3
  6. concentrationconcentrated
  7. customThe crude reaction product
  8. customwas triturated with diethyl ether (25 mL)
  9. filtrationfiltered
  10. customThe resulting solid (2.0 g, 83%) was collected

Sources & evidence

ORD record
ord-3beb65b7b55f4706bc34d90659a60ca4
Source dataset
uspto-grants-2005_05
Patent number
US06887996B2

Reaction notes

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