Potassium Carbonate → Ethyl 3-(5-bromo-2-thioureidopyridin-4-yloxy)-4-chlorobenzoate

HRID 911037Notes

Reaction equation

C([NH:9][C:10](=[S:32])[NH:11][C:12]1[CH:17]=[C:16]([O:18][C:19]2[CH:20]=[C:21]([CH:27]=[CH:28][C:29]=2[Cl:30])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:15]([Br:31])=[CH:14][N:13]=1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Br:31][C:15]1[C:16]([O:18][C:19]2[CH:20]=[C:21]([CH:27]=[CH:28][C:29]=2[Cl:30])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][C:12]([NH:11][C:10]([NH2:9])=[S:32])=[N:13][CH:14]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A flask was charged with ethyl 3-(2-(3-benzoylthioureido)-5-bromopyridin-4-yloxy)-4-chlorobenzoate (1.37 g, 2.56 mmol), Potassium carbonate (0.496 g, 3.59 mmol) and ethanol (50 mL). The reaction mixture was stirred at 40° C. for 6 hours and then concentrated. The crude material was purified by silica gel column chromatography eluting with 10% ethyl acetate in hexanes to give the desired product (0.61 g, 54% yield) as white solid.

Workup

concentrationconcentrated
customThe crude material was purified by silica gel column chromatography
washeluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-200ea46c0d54421c98b45f0b14ce1a51
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022222B2

Reaction notes

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