Cesium carbonate → HCID 59618406, compound

HRID 449905

Reaction equation

HRID 449905 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][C:12](=[O:23])[C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]#[N:21])=[CH:15][C:14]=2[Cl:22])[CH:5]=[CH:4][N:3]=1.[CH3:24][C:25]1[N:30]=[C:29]([NH2:31])[CH:28]=[C:27]([CH3:32])[N:26]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)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].COCCOC.O1CCOCC1>[Cl:22][C:14]1[CH:15]=[C:16]([C:20]#[N:21])[CH:17]=[C:18]([Cl:19])[C:13]=1[C:12]([NH:11][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:31][C:29]2[CH:28]=[C:27]([CH3:32])[N:26]=[C:25]([CH3:24])[N:30]=2)[C:7]=1[N+:8]([O-:10])=[O:9])=[O:23]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 680392,6-Dimethyl-4-aminopyrimidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86648955N-(2-chloro-3-nitropyridin-4-yl)-2,6-dichloro-4-cyanobenzamide

Product 1

HCID 59618406HCID 59618406, compoundYield 5%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 80711,2-DimethoxyethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A 25 mL microwave tube containing N-(2-chloro-3-nitropyridin-4-yl)-2,6-dichloro-4-cyanobenzamide (100 mg, 0.27 mmol), 2,6-dimethylpyrimidin-4-amine (43 mg, 0.35 mmol), Pd2(dba)3 (8 mg, 0.009 mmol), Cs2CO3 (180 mg, 0.54 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, 4 mg, 0.005 mmol), dioxane (8 mL) and DME (3 mL) was degassed and then charged by N2 (3×). The mixture was then irradiated in a microwave reactor at 160° C. for 2 hours and then diluted with dioxane (20 mL). The reaction was filtered through Celite and concentrated under reduced pressure. The residue was purified by reverse-phase HPLC (Gemini, 200 mm×25 mm, gradient: CH3CN/0.05% NH3.H2O, 50-80, 10 min) to afford the desired product (4 mg, yield: 5%). LCMS (ESI) m/z: 458.3 [M+H+].

Workup

  1. customwas degassed
  2. additioncharged by N2 (3×)
  3. customThe mixture was then irradiated in a microwave reactor at 160° C. for 2 hours
  4. additiondiluted with dioxane (20 mL)
  5. filtrationThe reaction was filtered through Celite
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by reverse-phase HPLC (Gemini, 200 mm×25 mm, gradient: CH3CN/0.05% NH3.H2O, 50-80, 10 min)

Sources & evidence

ORD record
ord-650efcb8aa104dc69f9c83da8e541b8c
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Linked notes

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