Potassium Phosphate, Tribasic → 4-Cyclopropyl-N-methylaniline

HRID 63647Notes

Reaction equation

HRID 63647 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.[CH:10]1(B(O)O)[CH2:12][CH2:11]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:10]1([C:2]2[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=2)[CH2:12][CH2:11]1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2757052Benzenamine, 4-bromo-N-methyl-HCID 2760897Cyclopropylboronic acid

Product 1

HCID 153651924-Cyclopropyl-N-methylanilineYield 68%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a suspension of 4-bromo-N-methylaniline (500 mg, 2.69 mmol), cyclopropylboronic acid (462 mg, 5.38 mmol), (cyclohexyl)3P+HBF4− (99 mg, 0.27 mmol) and K3PO4 (2.0 g, 9.4 mmol) in toluene (20 mL) and H2O (1 mL) was added Pd(OAc)2 (36 mg, 0.16 mmol) at r.t. under N2. The reaction was stirred at reflux overnight. The reaction was filtered, concentrated, and purified by silica gel chromatography (PE:EtOAc=10:1) to give 268 mg (68%) of the title compound as a brown oil. [M+H] Calc'd for C10H23N, 148. Found, 148.

Workup

  1. temperatureat reflux overnight
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (PE:EtOAc=10:1)

Sources & evidence

ORD record
ord-a03e03868c984fbcb98c3d1ffc13029b
Source dataset
uspto-grants-2016_09
Patent number
US09447046B2

Reaction notes

Loading…