m-Chloroperbenzoic acid → 4-bromo-1-(2-methylsulfinyl-pyrimidin-4-yl)-1H-indole

HRID 1516440노트

반응식

HRID 1516440 반응식
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C:11]1[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=1.C1C=C(Cl)C=C(C(OO)=[O:27])C=1.CCOC(C)=O.CCCCCC>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C:11]1[CH:16]=[CH:15][N:14]=[C:13]([S:17]([CH3:18])=[O:27])[N:12]=1

참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 21226206Ethyl acetate hexaneHCID 581379584-bromo-1-(2-(methylthio)pyrimidin-4-yl)-1H-indole

생성물 1

HCID 674343154-bromo-1-(2-methylsulfinyl-pyrimidin-4-yl)-1H-indole수율 94.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of 4-bromo-1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indole (5.0 g) in DCM (200 mL) at 0° C. was added MCPBA (4.01 g) in portions, and the mixture stirred at 0° C. for 1 h. The reaction mixture was quenched in 10% Na2SO3 (aq), partitioned between DCM and NaHCO3 (aq), the organic layer washed with NaHCO3 (aq), and dried over Na2SO4. The solvent was stripped to provide a light yellow solid, which was then treated with hot EtOAc/hexane (50:50), filtered, dried to provide 4-bromo-1-(2-methylsulfinyl-pyrimidin-4-yl)-1H-indole (4.98 g) as an off-white powder.

후처리

  1. customThe reaction mixture was quenched in 10% Na2SO3 (aq)
  2. custompartitioned between DCM and NaHCO3 (aq)
  3. washthe organic layer washed with NaHCO3 (aq)
  4. dry with materialdried over Na2SO4
  5. customto provide a light yellow solid, which
  6. filtrationfiltered
  7. customdried

출처 및 근거

ORD 기록
ord-6f950d9fb35a4e35a8c8a8470c1c5c25
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227478B2

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