Potassium Carbonate → HCID 67469543, compound

HRID 1522551Notes

Reaction equation

HRID 1522551 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>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:9][C:10]1[CH:15]=[C:14]([C:2]2[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=2)[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 844322-Chloropyridin-4-amineHCID 2734323(3-Chlorophenyl)boronic acid

Product 1

HCID 67469543HCID 67469543, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

2-Chloropyridin-4-amine (200 mg, 1.556 mmol), 3-chlorophenylboronic acid (243 mg, 1.556 mmol) and Pd(PPh3)4 (450 mg, 0.389 mmol) were combined in dioxane (4 mL) and saturated K2CO3 solution (2 mL). The mixture was heated at 120° C. for 30 minutes in a microwave. The solvent was removed to give a residue which was purified by silica column chromatography eluting with a gradient of 0-5% methanol in dichloromethane to give the title compound as light yellow oil (150 mg, 47.1% yield).

Workup

  1. customThe solvent was removed
  2. customto give a residue which
  3. customwas purified by silica column chromatography
  4. washeluting with a gradient of 0-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-897ea2604099421bb859140562955355
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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