Water → 3-(5-Chloro-2-methoxyphenyl)pyridin-4-amine

HRID 634547Notes

Reaction equation

HRID 634547 reaction equation
I[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:19][CH3:20])=[C:14](B(O)O)[CH:15]=1.C([O-])([O-])=O.[K+].[K+].O>C1(C)C=CC=CC=1.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.C(O)C>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([O:19][CH3:20])=[C:12]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[NH2:8])[CH:11]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15165104-Amino-3-iodopyridineHCID 27357515-Chloro-2-methoxyphenylboronic acid

Product 1

HCID 509670043-(5-Chloro-2-methoxyphenyl)pyridin-4-amine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

3-iodopyridin-4-amine (2.2 g, 10 mmol), (5-chloro-2-methoxyphenyl)boronic acid (1.86 g, 10 mmol) and, and K2CO3 (4.2 g, 30 mmol) were mixed in 50 mL of toluene, 5 mL of deionized water and 5 mL of ethanol. To the solution was bubbled with nitrogen for 15 min. Pd(PPh3)4 (0.23 g, 0.2 mmol) was then added. The mixture was refluxed overnight under nitrogen. After cooling, the aqueous layer was removed and the organic layer was then concentrated. The residue was then purified by column chromatography using ethyl acetate as the eluent. 2.0 g (85%) of product was collected as the product.

Workup

  1. customTo the solution was bubbled with nitrogen for 15 min
  2. temperatureThe mixture was refluxed overnight under nitrogen
  3. temperatureAfter cooling
  4. customthe aqueous layer was removed
  5. concentrationthe organic layer was then concentrated
  6. customThe residue was then purified by column chromatography
  7. custom2.0 g (85%) of product was collected as the product

Sources & evidence

ORD record
ord-638d4d080b8c4ebf93b1589b2afe3f2d
Source dataset
uspto-grants-2016_04
Patent number
US09324949B2

Reaction notes

Loading…