Cesium carbonate → HCID 117779002, compound

HRID 2206515Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[N:27][CH:28]=1>CN(C)C=O>[CH3:1][C:2]1[N:3]([CH2:22][C:23]2[CH:24]=[N:25][CH:26]=[N:27][CH:28]=2)[C:4]2[C:9]([C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 2-methyl-1H-indole-3-carboxylate (0.5 g, 2.6 mmol) in N,N-dimethylformamide (20 mL) was added cesium carbonate (1.7 g, 5.2 mmol) and 5-(bromomethyl)pyrimidine (0.3 g, 1.7 mmol). The mixture was stirred at 100° C. for 1 hour and then concentrated to give a residue. The residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:20) to give methyl 2-methyl-1-(pyrimidin-5-ylmethyl)-1H-indole-3-carboxylate (110 mg, 14%)

Workup

concentrationconcentrated
customto give a residue
customThe residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:20)

Sources & evidence

ORD record: ord-8379a546236843f8a5fe86a963cbfa1f
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371331B2

Reaction notes

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