Potassium Phosphate, Tribasic → 2,6-Dichloro-5-cyclopropylnicotinonitrile

HRID 2284492Notes

Reaction equation

HRID 2284492 reaction equation
[Cl:1][C:2]1[N:9]=[C:8]([Cl:10])[C:7](I)=[CH:6][C:3]=1[C:4]#[N:5].[CH:12]1(B(O)O)[CH2:14][CH2:13]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].P(C1CCCCC1)(C1CCCCC1)C1CCCCC1>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2].O>[Cl:1][C:2]1[N:9]=[C:8]([Cl:10])[C:7]([CH:12]2[CH2:14][CH2:13]2)=[CH:6][C:3]=1[C:4]#[N:5]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 848199372,6-Dichloro-5-iodonicotinonitrile

Product 1

HCID 848199202,6-Dichloro-5-cyclopropylnicotinonitrileYield 70.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 22272177Toluene waterSolvent

Procedure

A mixture of compound 2,6-dichloro-5-iodonicotinonitrile (10 g, 33.4 mmol), cyclopropylboronic acid (3.5 g, 40.1 mmol), K3PO4 (28 g, 133.6 mmol), Cy3P (1 g, 3.3 mmol) and Pd(OAc)2 (0.5 g, 2.2 mmol) in Toluene/H2O (300 mL/15 mL) was stirred under refluxing overnight. The mixture was poured into water and extracted with EtOAc. The separated organics was dried, concentrated and purified by column chromatography (Petroleum ether:EtOAc=10:1) to give compound 2,6-dichloro-5-cyclopropylnicotinonitrile (5 g, 70%). 1H-NMR (400 MHz, CDCl3) δ (ppm) 7.43 (s, 1H), 2.08 (m, 1H), 1.18 (m, 2H), 0.69 (m, 2H)

Workup

  1. temperatureunder refluxing overnight
  2. extractionextracted with EtOAc
  3. customThe separated organics was dried
  4. concentrationconcentrated
  5. custompurified by column chromatography (Petroleum ether:EtOAc=10:1)

Sources & evidence

ORD record
ord-70a30f44af9f438a8e4a022f0bb94227
Source dataset
uspto-grants-2015_09
Patent number
US09145429B2

Reaction notes

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