Potassium Phosphate, Tribasic → 5-Cyclopropylpyridin-3-amine

HRID 2283670Notes

Reaction equation

HRID 2283670 reaction equation
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:35]1[CH:36]=[C:37]([NH2:41])[CH:38]=[N:39][CH:40]=1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(OCC)(=O)C>[NH2:41][C:37]1[CH:38]=[N:39][CH:40]=[C:35]([CH:1]2[CH2:3][CH2:2]2)[CH:36]=1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 8176813-Amino-5-bromopyridineHCID 2760897Cyclopropylboronic acid

Product 1

HCID 665204195-Cyclopropylpyridin-3-amine

Reagents, catalysts & solvents 4

HCID 8895Cupric acetateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of cyclopropyl boronic acid (497 mg), palladium acetate (II) (65 mg), tricyclohexylphosphine (162 mg), and potassium phosphate (2.5 g) in toluene (9 mL) and water (0.45 mL) was added to 5-bromopyridin-3-amine (500 mg), and the mixture was stirred at 100° C. for 11 hours. Ethyl acetate and water were added, the organic layer was separated, and the resultant was washed with a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain 3-amino-5-cyclopropylpyridine.

Workup

  1. customthe organic layer was separated
  2. washthe resultant was washed with a saturated saline solution
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. customthe solvent was evaporated under vacuum
  5. customThe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-906001ab8f3e4c6ca42e53c88ee5a869
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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