Sodium Carbonate → 4-(3,4-Dichloro-phenyl)-pyridine-2,6-diamine

HRID 277092Notes

Reaction equation

HRID 277092 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Br)[CH:5]=[C:4]([NH2:9])[N:3]=1.[Cl:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][C:16]=1[Cl:17].C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.[CH-]1C=C(P(C2C=CC=CC=2)C2C=CC=CC=2)C=C1.[CH-]1C=C(P(C2C=CC=CC=2)C2C=CC=CC=2)C=C1.Cl[Pd]Cl.[Fe+2]>[Cl:10][C:11]1[CH:12]=[C:13]([C:6]2[CH:7]=[C:2]([NH2:1])[N:3]=[C:4]([NH2:9])[CH:5]=2)[CH:14]=[CH:15][C:16]=1[Cl:17]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343303,4-Dichlorobenzeneboronic acidHCID 114353934-Bromo-2,6-diaminopyridine

Product 1

HCID 226297234-(3,4-Dichloro-phenyl)-pyridine-2,6-diamine

Reagents, catalysts & solvents 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 40.5 mg (0.21 mmol) 2,6-diamino-4-bromo-pyridine, 90.5 mg (0.47 mmol) 3,4-dichloro-phenyl-boronic acid, 7.8 mg (0.01 mmol) Dichloro(1,1′-bis(diphenylphosphino) ferrocene)palladium (II) dichloromethane adduct and 0.3 ml 2M Na2CO3 in 1 ml dimethoxyethane was heated to 80° C. for 17 h. The mixture was filtered over silica washed with MeOH/DCM and concentrated. The residue was taken up in 1 ml DMF and the totle compound was purified by reversed phase column chromatography eluting wit an acetonitrile/water gradient to yield 29 mg (52%), MS m/e (%): 254 M+ (100).

Workup

  1. filtrationThe mixture was filtered over silica
  2. washwashed with MeOH/DCM
  3. concentrationconcentrated
  4. customthe totle compound was purified by reversed phase column chromatography
  5. washeluting wit an acetonitrile/water gradient
  6. customto yield 29 mg (52%), MS m/e (%)

Sources & evidence

ORD record
ord-77b5c055a48d483a9344df34f173807e
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Reaction notes

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