Potassium Phosphate, Tribasic → HCID 178419857, compound

HRID 1842476Notes

Reaction equation

HRID 1842476 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]2[NH:6][C:7]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:8][C:4]=2[CH:3]=1.[CH:17]1(B(O)O)[CH2:19][CH2:18]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O>[CH:17]1([C:2]2[CH:16]=[CH:15][C:5]3[NH:6][C:7]([CH:9]4[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]4)=[N:8][C:4]=3[CH:3]=2)[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 178419323HCID 178419323, compound

Product 1

HCID 178419857HCID 178419857, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

The mixture of 5-bromo-2-piperidin-4-yl-1H-benzoimidazole (200 mg, 0.53 mol), cyclopropanylboronic acid (58.4 mg, 0.687 mmol), K3PO4 (391 mg, 1.85 mmol), Pd (OAc)2 (6.8 mg, 0.005 mmol) and tricyclohexylphosphine (14.9 mg, 0.053 mmol) in toluene (10 mL) and H2O (3 mL) was stirred at 90° C. under N2 for 12 h. Then it was poured into H2O and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated to give the crude product which was purified by column chromatography (ethyl acetate:petroleum ether=1:2) to give the compound 5-Cyclopropyl-2-piperidin-4-yl-1H-benzoimidazole (58 mg, 30%) as white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customto give the crude product which
  5. customwas purified by column chromatography (ethyl acetate:petroleum ether=1:2)

Sources & evidence

ORD record
ord-85baf849f2b3485a8508f695000580a8
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

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