Water → HCID 59813119, compound

HRID 448145Notes

Reaction equation

HRID 448145 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[CH:12]1(B(O)O)[CH2:14][CH2:13]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:26]1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[OH2:45]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:45][CH3:26])[CH:10]=2)[C:5]([CH:12]2[CH2:14][CH2:13]2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 962Water2×HCID 86401-NaphthylamineHCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acid

Product 1

HCID 59813119HCID 59813119, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of aminonaphthalene f (1 g, 4.0 mmol), cyclopropyl boronic acid (438 mg, 5.1 mmol), potassium phosphate (2.97 g, 14 mmol) and tricyclohexylphosphine (112 mg, 0.4 mmol) in toluene (21 mL) and water (0.8 mL) under nitrogen atmosphere was added palladium acetate (45 mg, 0.2 mmol) with vigorous stirring. The mixture was heated to 100° C. for 3 h and then cooled to room temperature. Water was added and the mixture extracted with ethyl acetate, dried over sodium sulfate and concentrated.

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-674d5d9f403d413b9660b1b5cb8724eb
Source dataset
uspto-grants-2013_07
Patent number
US08481581B2

Reaction notes

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