Potassium Phosphate, Tribasic → HCID 67980662, compound

HRID 1427518Notes

Reaction equation

HRID 1427518 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[CH3:9].[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=2[CH3:9])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 742994-Chlorophenylboronic acidHCID 122956076-Chloro-5-methylpyridin-3-amine

Product 1

HCID 67980662HCID 67980662, compoundYield 57.2%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 6-chloro-5-methylpyridin-3-amine (3 g, 20 mmol) in 1,2-dimethoxyethane (30 mL) was added PdCl2(dppf) (770 mg, 1.16 mmol), 4-chlorophenylboronic acid (4.94 g, 31.6 mmol), and K3PO4 (8.93 g, 42.1 mmol). The reaction mixture was purged with nitrogen and heated to reflux. Water (20 mL) was added and the reaction mixture was stirred at reflux for 48 h. The reaction mixture was extracted with ethyl acetate (30 mL*3). The combined organic layers were concentrated under reduced pressure. Purification by silica gel chromatography provided 6-(4-chlorophenyl)-5-methylpyridin-3-amine (2.5 g) as a yellow solid. 1HNMR (400 MHz, CDCl3) δ 7.96 (s, 1H), 7.30-7.36 (m, 4H), 6.83 (s, 1H), 2.21 (s, 3H).

Workup

  1. customThe reaction mixture was purged with nitrogen
  2. temperatureheated to reflux
  3. additionWater (20 mL) was added
  4. temperatureat reflux for 48 h
  5. extractionThe reaction mixture was extracted with ethyl acetate (30 mL*3)
  6. concentrationThe combined organic layers were concentrated under reduced pressure
  7. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-f0cc4d9ac5254dcca6a886b61fa52455
Source dataset
uspto-grants-2015_01
Patent number
US08933104B2

Reaction notes

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