Cesium carbonate → 4-((4-Chlorobenzyl)amino)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one

HRID 2203018Notes

Reaction equation

HRID 2203018 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([CH3:20])=[C:15]([CH:17]4[CH2:19][CH2:18]4)[N:16]=3)[CH:13]=2)[C:4](=[O:21])[CH:3]=1.[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=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].O.CC(N(C)C)=O>[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH:28][C:2]2[CH:7]=[CH:6][N:5]([C:8]3[CH:9]=[CH:10][C:11]4[N:12]([C:14]([CH3:20])=[C:15]([CH:17]5[CH2:19][CH2:18]5)[N:16]=4)[CH:13]=3)[C:4](=[O:21])[CH:3]=2)=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 660364-ChlorobenzylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 1213862044-Bromo-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-2(1h)-pyridinone

Product 1

HCID 896905404-((4-Chlorobenzyl)amino)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-oneYield 20.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-bromo-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one (80 mg), 4-chlorobenzylamine (49.4 mg), xantphos (10.8 mg), tris(dibenzylideneacetone)dipalladium(0) (5.3 mg), cesium carbonate (151 mg) and DMA (2 ml) was heated at 120° C. for 30 min under microwave irradiation. The reaction mixture was cooled to room temperature, poured into water and extracted with EtOAc-THF. The extract was washed with brine, dried over MgSO4, concentrated and purified by NH silica gel column chromatography (hexane/EtOAc then EtOAc/MeOH) to give the title compound (19.1 mg) as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc-THF
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified by NH silica gel column chromatography (hexane/EtOAc

Sources & evidence

ORD record
ord-ba10fc58a121404798d7f084f2035206
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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