Cesium carbonate → 2-Chloro-5-cyclopropylpyridine

HRID 63653

Reaction equation

HRID 63653 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH:9]1(B(O)O)[CH2:11][CH2:10]1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:8][C:5]1[CH:4]=[CH:3][C:2]([CH:9]2[CH2:11][CH2:10]2)=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27344145-Bromo-2-chloropyridineHCID 2760897Cyclopropylboronic acid

Product 1

HCID 509888582-Chloro-5-cyclopropylpyridineYield 57.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 5-bromo-2-chloropyridine (990 mg, 5.15 mmol), cyclopropylboronic acid (893 mg, 10.39 mmol) and Cs2CO3 (5.082 g, 15.45 mmol) in 1,4-dioxane (25 mL) was added Pd(PPh3)4 (601 mg, 0.52 mmol) at r.t. under N2. The reaction was stirred at 100° C. for 1 h. After filtration, the solvent was removed in vacuo, and the residue was purified by silica gel chromatography (PE:EtOAc=50:1) to give 452 mg (57%) of the title compound as a colorless oil. [M+H] Calc'd for C8H8NCl, 154. Found, 154.

Workup

  1. filtrationAfter filtration
  2. customthe solvent was removed in vacuo
  3. customthe residue was purified by silica gel chromatography (PE:EtOAc=50:1)

Sources & evidence

ORD record
ord-52ed6b39f3aa48a795435627d53ab571
Source dataset
uspto-grants-2016_09
Patent number
US09447046B2

Linked notes

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