1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → (5-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

HRID 1011239Notes

Reaction equation

HRID 1011239 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.[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)[CH2:15][CH2:14]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].ClCCl>[Cl:8][C:5]1[N:4]2[N:9]=[CH:10][N:11]=[C:3]2[C:2]([NH:25][C:22]2[CH:21]=[CH:20][C:19]([N:16]3[CH2:15][CH2:14][N:13]([CH3:12])[CH2:18][CH2:17]3)=[CH:24][CH:23]=2)=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 23676156Sodium t-butoxideHCID 576643738-Bromo-5-chloro-[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 57664356(5-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amineYield 64.4%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6344DichloromethaneSolventHCID 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-(4-methyl-piperazin-1-yl)-phenylamine (91 mg, 0.47 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 irradiated in a sealed tube in a microwave (CEM Explorer) under a nitrogen atmosphere for 45 minutes at 110° C. After addition of dichloromethane the suspension is filtered through a plug of silica and the filtrate evaporated and stripped twice with dichloromethane. The residue is purified by flash chromatography (silica gel, dichloromethane/7N NH3 in methanol 95:5) affording the title compound (95 mg) as a foam.

Workup

  1. customirradiated in a sealed tube in a microwave (CEM Explorer) under a nitrogen atmosphere for 45 minutes at 110° C
  2. filtrationis filtered through a plug of silica
  3. customthe filtrate evaporated
  4. customThe residue is purified by flash chromatography (silica gel, dichloromethane/7N NH3 in methanol 95:5)

Sources & evidence

ORD record
ord-104d4ab6553d416c80f7b816bcb58aac
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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