Benzenamine, 4-(4-morpholinyl)- → 5-chloro-N-(4-morpholinophenyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine

HRID 1011238Notes

Reaction equation

HRID 1011238 reaction equation
Br[C:2]1[C:3]2[N:4]([N:9]=[CH:10][N:11]=2)[C:5]([Cl:8])=[CH:6][CH:7]=1.[N:12]1([C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.CC(C)([O-])C.[Na+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:8][C:5]1[N:4]2[N:9]=[CH:10][N:11]=[C:3]2[C:2]([NH:24][C:21]2[CH:20]=[CH:19][C:18]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:23][CH:22]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 576643738-Bromo-5-chloro-[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 576643685-chloro-N-(4-morpholinophenyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amineYield 30.8%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 8-bromo-5-chloro-[1,2,4]triazolo[1,5-a]pyridine (160 mg, 0.69 mmol), 4-morpholin-4-yl-phenylamine (135 mg, 0.76 mmol), sodium-tert-butoxide (93 mg, 0.96 mmol), tris(dibenzylideneacetone)dipalladium (0) (13 mg, 13.76 μmol) and Xantphos (16 mg, 27.52 μmol) in dry toluene is heated at 90° C. in a sealed tube under a nitrogen atmosphere for 16 hours. The reaction mixture is evaporated to dryness and the residue partitioned between dichloromethane and 10% aqueous citric acid. The organic phase is further washed with water (1×) and brine (1×), dried over magnesium sulfate, filtered and evaporated. The solid residue (207 mg) is purified by flash chromatography (silica gel, dichloromethane/methanol 97:3) affording the title compound (70 mg) as a solid.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. customthe residue partitioned between dichloromethane and 10% aqueous citric acid
  3. washThe organic phase is further washed with water (1×) and brine (1×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe solid residue (207 mg) is purified by flash chromatography (silica gel, dichloromethane/methanol 97:3)

Sources & evidence

ORD record
ord-b678bad2c4a54d2c88c86baa7a19af51
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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