Cesium carbonate → 6-Methoxy-2-(4-nitrophenyl) benzothiazole

HRID 643644Notes

Reaction equation

Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.I[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(P(CCCC)CCCC)CCC>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu](Br)Br>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)[S:3][C:4]=2[CH:10]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Under N2, in a sealed tube, to 22 (19.7 mmol) in DMF 50 ml, 1-iodo-4-nitrobenzene (21.6 mmol), cesium carbonate (19.6 mmol), palladium acetate (0.98 mmol), copper bromide (0.2 mmol) and tributylphosphine (1.9 mmol) were added. The reaction was stirred at 150° C. overnight and, after cooling to room temperature, the mixture was extracted with ethyl acetate. The organic layer was then washed (3 times) with water, dried over Na2SO4 and the solvent removed via a rotary evaporator. The residue was purified by chromatography on silica gel using 9:1 hexane/ethyl acetate as the eluent to yield 4.62 g (81%) of 23 as a yellow solid.

Workup

temperatureafter cooling to room temperature
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was then washed (3 times) with water
dry with materialdried over Na2SO4
customthe solvent removed via a rotary evaporator
customThe residue was purified by chromatography on silica gel using 9:1 hexane/ethyl acetate as the eluent

Sources & evidence

ORD record: ord-71638f10d91c4d9fa9472f05e98690d4
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700616B2

Reaction notes

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