(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → 6-Iodo-4-methoxy-3-(5-methyl-oxazol-2-yl)-quinoline

HRID 1297637Notes

Reaction equation

O=[C:2]([CH3:20])[CH2:3][NH:4][C:5]([C:7]1[CH:8]=[N:9][C:10]2[C:15]([C:16]=1[O:17][CH3:18])=[CH:14][C:13]([I:19])=[CH:12][CH:11]=2)=[O:6].[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>C1COCC1>[I:19][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:5]1[O:6][C:2]([CH3:20])=[CH:3][N:4]=1)=[C:16]2[O:17][CH3:18]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 6-iodo-4-methoxy-quinoline-3-carboxylic acid (2-oxo-propyl)-amide (example 16b) (1.3 g, 3.38 mmol) and Burgess Regent ((methoxycarbonylsulfamoyl)-triethylammonium hydroxide, inner salt) (2.0 g, 8.5 mmol) in THF was heated to 150° C. for 15 min by microwave. The solvent was removed by rotary evaporator. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 0%-50% ethyl acetate in hexanes in 30 min) afforded 6-iodo-4-methoxy-3-(5-methyl-oxazol-2-yl)-quinoline (0.49 g, 40%) as a white solid. LC-MS m/e 367 (MH+).

Workup

customThe solvent was removed by rotary evaporator

Sources & evidence

ORD record: ord-7b51d73eed4740cdb192085abc77e32d
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250515B2

Reaction notes

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