Tetrahydrofuran → HCID 89690343, compound

HRID 2203019Notes

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:33]=[CH:32][C:26](/[CH:27]=[CH:28]/B(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].C1COCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[Cl:22][C:23]1[CH:33]=[CH:32][C:26](/[CH:27]=[CH: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

Conditions

Temperature: 70 °C

Procedure

A mixture of 4-bromo-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one (178 mg), (E)-(4-chlorostyryl)boronic acid (189 mg), potassium carbonate (214 mg), PdCl2(dppf) (18.9 mg), THF (3 ml) and water (1 ml) was heated at 70° C. under N2 atmosphere overnight. The mixture was partitioned between EtOAc and water, and the organic layer was washed with brine, dried over MgSO4, concentrated in vacuo, and purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (80 mg) as a solid.

Workup

customThe mixture was partitioned between EtOAc and water
washthe organic layer was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
custompurified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record: ord-b25579f0485b4e718303ce0c6710cd15
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

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