Cesium carbonate → HCID 59618525, compound

HRID 449880Notes

Reaction equation

HRID 449880 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:18])[C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])[CH:5]=[CH:4][N:3]=1.Cl[C:20]1[N:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[N:21]=1.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.C([O-])([O-])=O.[Cs+].[Cs+]>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].O1CCOCC1>[Cl:16][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:17])[C:10]=1[C:9]([NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:20]2[N:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[N:21]=2)[CH:7]=1)=[O:18]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 205502-Chloro-4,6-dimethylpyrimidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59618313N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide

Product 1

HCID 59618525HCID 59618525, compoundYield 8%

Reagents, catalysts & solvents 2

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

Procedure

To a microwave tube was added N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide (0.25 g, 0.89 mmol), 2-chloro-4,6-dimethylpyrimidine (0.19 g, 1.34 mmol), Pd2(dba)3 (0.81 g, 0.089 mmol), XantPhos (0.104 g, 0.179 mmol), Cs2CO3 (0.85 g, 2.6 mmol) and dioxane (4 mL). The mixture was degassed with N2 for 10 min. The resulting mixture was irradiated in a microwave reactor at 140° C. for 3 hours and then cooled to room temperature. The mixture was filtered through Celite and concentrated under reduced pressure. The residue was purified by column chromatography to afford the desired product as a white solid (22 mg, yield: 8%). 1H NMR (500 MHz, MeOH-d4): δ 8.96 (d, J=1.5 Hz, 1H), 8.17 (d, J=5.5 Hz, 1H), 7.41-7.54 (m, 4H), 6.77 (s, 1H), 2.44 (s, 6H). LCMS (ESI) m/z: 388.0 [M+H+].

Workup

  1. customThe mixture was degassed with N2 for 10 min
  2. customThe resulting mixture was irradiated in a microwave reactor at 140° C. for 3 hours
  3. filtrationThe mixture was filtered through Celite
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-aeb40538d31b48fe9fbc58fb59472631
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

Loading…