Cesium carbonate → methyl 1-(thiazol-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

HRID 624668Notes

Reaction equation

[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]1.Br[C:15]1[S:16][CH:17]=[CH:18][N:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1>[S:16]1[CH:17]=[CH:18][N:19]=[C:15]1[N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of methyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate (200 mg, 1.135 mmol), 2-bromothiazole (205 μl, 2.271 mmol) and cesium carbonate (1110 mg, 3.41 mmol) in NMP (1135 μl) was heated at 130° C. for 2 h. The mixture was then purified by HPLC to afford the title compound as a brownish-white solid.

Workup

customThe mixture was then purified by HPLC

Sources & evidence

ORD record: ord-9cb94a1a285841d7a6191a7984af8102
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303045B2

Reaction notes

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