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

HRID 643644노트

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HRID 643644 반응식
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

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 124951-Iodo-4-nitrobenzeneHCID 13831TributylphosphineHCID 112187652-Bromo-6-methoxy-1,3-benzothiazole

생성물 1

HCID 106608526-Methoxy-2-(4-nitrophenyl) benzothiazole수율 81.9%

시약·촉매·용매 3

HCID 24611Copper bromide (CuBr2)촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

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온도
150 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-71638f10d91c4d9fa9472f05e98690d4
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700616B2

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