Cesium carbonate → 4-(((5-Chloro-2-thienyl)methyl)amino)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one

HRID 2203009Notes

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[S:27][C:26]([CH2:28][NH2:29])=[CH:25][CH:24]=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].O.CC(N(C)C)=O>[Cl:22][C:23]1[S:27][C:26]([CH2:28][NH:29][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

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 (30 mg), 1-(5-chloro-2-thienyl)methanamine (20 mg), tris(dibenzylideneacetone)dipalladium(0) (2.0 mg), cesium carbonate (57 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (3 mg) and DMA (0.4 ml) was heated at 120° C. for 1 h under microwave irradiation. To this mixture was added water, and the precipitate was collected by filtration. The resulting solid was recrystallized from EtOAc-hexane-EtOH to give the title compound (8.6 mg) as a yellow solid.

Workup

filtrationthe precipitate was collected by filtration
customThe resulting solid was recrystallized from EtOAc-hexane-EtOH

Sources & evidence

ORD record: ord-a3869e2f19b04b62ab8c6466e31f836b
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

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