Potassium Phosphate, Tribasic → HCID 67980662, compound

HRID 2173874Notes

Reaction equation

HRID 2173874 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-4602e7e340a2425a81748ad9821b082b
Source dataset
uspto-grants-2015_06
Patent number
US09056834B2

Reaction notes

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