Dimethyl Disulfide → 7-(Methylsulfanyl)-1H-indole

HRID 2042346노트

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HRID 2042346 반응식
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[Li]C(C)(C)C.[CH3:16][S:17]SC>C1COCC1>[CH3:16][S:17][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2

참가 물질

5

반응물 3

HCID 12232Dimethyl DisulfideHCID 27570207-BromoindoleHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 198489667-(Methylsulfanyl)-1H-indole수율 56.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 7-bromo-1H-indole (3.0 g, 15.3 mmol) in THF (60 mL) at −78° C. was added tBuLi (1.7 M, 33.8 mL, 57.4 mmol) and the mixture was allowed to warm to 0° C. The reaction was re-cooled to −78° C. and a solution of dimethyl disulfide (2.0 mL, 22.9 mmol) was added and the reaction was allowed to warm to 0° C. The reaction was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to yield the crude product. This material was purified by chromatography over silica gel eluting with ethyl acetate in hexanes (0→2%) to afford pure 7-(methylthio)-1H-indole (1.4 g, 55%). 1H NMR (400 MHz, CDCl3) δ=2.50 (s, 3 H), 6.58 (dd, J=3.03, 2.02 Hz, 1H), 7.09 (t, J=7.58 Hz, 1H), 7.18-7.31 (m, 2H), 7.56 (d, J=7.83 Hz, 1H), 8.45 (br. s., 1 H); MS (ES+): m/z 164.15 [MH+].

후처리

  1. temperatureThe reaction was re-cooled to −78° C.
  2. temperatureto warm to 0° C
  3. customThe reaction was quenched with saturated ammonium chloride
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customto yield the crude product
  9. customThis material was purified by chromatography over silica gel eluting with ethyl acetate in hexanes (0→2%)

출처 및 근거

ORD 기록
ord-ad84f14b226f4709821bd71d086f65ce
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586546B2

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