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

HRID 2042346ノート

反応式

HRID 2042346 の反応式
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

参加物

5

反応物 3

HCID 12232Dimethyl DisulfideHCID 27570207-BromoindoleHCID 178418306HCID 178418306、化合物

生成物 1

HCID 198489667-(Methylsulfanyl)-1H-indole収率 56.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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+].

後処理

  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%)

出典と根拠

ORDレコード
ord-ad84f14b226f4709821bd71d086f65ce
出典データセット
uspto-grants-2013_11
特許番号
US08586546B2

反応ノート

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