4-amino-N-(pyridin-3-ylmethyl)benzamide → 4-(5-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-N-pyridin-3-ylmethyl-benzamide

HRID 1011241Notes

Reaction equation

HRID 1011241 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.[NH2:12][C:13]1[CH:28]=[CH:27][C:16]([C:17]([NH:19][CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[O:18])=[CH:15][CH:14]=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>O1CCOCC1.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:12][C:13]2[CH:28]=[CH:27][C:16]([C:17]([NH:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[O:18])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 5778334-amino-N-(pyridin-3-ylmethyl)benzamideHCID 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 576643524-(5-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-N-pyridin-3-ylmethyl-benzamideYield 71.8%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 8-bromo-5-chloro-[1,2,4]triazolo[1,5-a]pyridine (100 mg, 0.43 mmol), 4-Amino-N-pyridin-3-ylmethyl-benzamide (108 mg, 0.48 mmol), sodium-tert-butoxide (58 mg, 0.6 mmol), tris(dibenzylideneacetone)dipalladium (0) (39 mg, 40 μmol) and Xantphos (50 mg, 90 μmol) in dioxane is degassed for one minute by nitrogen bubbling and then irradiated in a sealed tube in a microwave (CEM Explorer) under a nitrogen atmosphere for 30 minutes at 110° C. The solvent is evaporated and the crude is dissolved in dichloromethane and filtered in order to remove the palladium catalyst. The residue is purified by flash chromatography (silica gel, dichloromethane/7N NH3 in methanol 95:5) affording the title compound (117 mg) as a solid.

Workup

  1. customirradiated in a sealed tube in a microwave (CEM Explorer) under a nitrogen atmosphere for 30 minutes at 110° C
  2. customThe solvent is evaporated
  3. dissolutionthe crude is dissolved in dichloromethane
  4. filtrationfiltered in order
  5. customto remove the palladium catalyst
  6. customThe residue is purified by flash chromatography (silica gel, dichloromethane/7N NH3 in methanol 95:5)

Sources & evidence

ORD record
ord-59b662cc73ee4a0c8764bd687c820646
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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