Cesium carbonate → HCID 58449351, compound

HRID 2278750Notes

Reaction equation

HRID 2278750 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=2)[CH:19]=1)[C:5]([NH:7][C@@H:8]([C:10]1[CH:11]=[N:12][C:13]([CH3:16])=[N:14][CH:15]=1)[CH3:9])=[O:6].[NH:27]1[CH2:31][CH2:30][CH2:29][C:28]1=[O:32].C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>CO.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]>[CH3:26][C:23]1[CH:24]=[CH:25][C:20]([C:18]2[CH:17]=[C:4]([CH:3]=[C:2]([N:27]3[CH2:31][CH2:30][CH2:29][C:28]3=[O:32])[CH:19]=2)[C:5]([NH:7][C@@H:8]([C:10]2[CH:11]=[N:12][C:13]([CH3:16])=[N:14][CH:15]=2)[CH3:9])=[O:6])=[N:21][CH:22]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 312751,4-DioxaneHCID 58449363HCID 58449363, compound

Product 1

HCID 58449351HCID 58449351, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolvent

Procedure

Into a 5 mL microwave vial was charged (R)-3-bromo-5-(5-methylpyridin-2-yl)-N-(1-(2-methylpyrimidin-5-yl)ethyl)benzamide (20 mg, 0.05 mmol), 2-pyrrolidinone (7 mg, 0.08 mmol) xantphos (3 mg, 0.005 mmol), tris(dibenzylideneacetone)dipalladium(0) (2 mg, 0.002 mmol), cesium carbonate (50 mg, 0.1 mmol), and 1,4-dioxane (0.8 mL). The mixture was subjected to microwave irradiation at 130° C. for 10 min. The cooled mixture was diluted with 3 mL of methanol and purified by reverse phase HPLC to afford the title compound.

Workup

  1. customirradiation at 130° C. for 10 min
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-4a678c8dc1214bed98208219314fee28
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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