Cesium carbonate → HCID 86648952, compound

HRID 449887Notes

Reaction equation

HRID 449887 reaction equation
Br[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:19][C:20]1[N:25]=[C:24]([NH2:26])[CH:23]=[C:22]([CH:27]([CH3:29])[CH3:28])[N:21]=1.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].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.COCCOC>[Cl:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([Cl:16])[C:10]=1[C:9]([NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:26][C:24]2[CH:23]=[C:22]([CH:27]([CH3:28])[CH3:29])[N:21]=[C:20]([Cl:19])[N:25]=2)[CH:7]=1)=[O:18]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 735550432-Chloro-6-isopropylpyriMidin-4-aMineHCID 75464886N-(2-Bromopyridin-4-yl)-2,6-dichlorobenzamide

Product 1

HCID 86648952HCID 86648952, compoundYield 117.7%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a microwave tube was added N-(2-bromopyridin-4-yl)-2,6-dichlorobenzamide (0.25 g, 0.72 mmol), 2-chloro-6-isopropylpyrimidin-4-amine (0.16 g, 0.94 mmol), Pd2(dba)3 (0.020 g, 0.022 mmol), XantPhos (0.008 g, 0.014 mmol), Cs2CO3 (0.47 g, 1.4 mmol) dioxane (20 mL) and DME (5 mL). The mixture was degassed with N2 for 10 min. The resulting mixture was irradiated in a microwave reactor at 130° C. for 2 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 (EtOAc/Petrolum ether=20/80 to 30/70) to give 2,6-dichloro-N-(2-(2-chloro-6-isopropylpyrimidin-4-ylamino)pyridin-4-yl)benzamide (370 mg, yield: 90%). LCMS (ESI) m/z: 436.0 [M+H+].

Workup

  1. customThe mixture was degassed with N2 for 10 min
  2. customThe resulting mixture was irradiated in a microwave reactor at 130° C. for 2 hours
  3. filtrationThe mixture was filtered through Celite
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (EtOAc/Petrolum ether=20/80 to 30/70)

Sources & evidence

ORD record
ord-1dc9c1dd59374bdf9455eee1c09050c4
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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