Sodium Sulfate → 7-Fluorotryptamine

HRID 1666898ノート

反応式

HRID 1666898 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][CH:14]=[C:13]2[CH:17]=[CH:18][N+:19]([O-])=O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[F:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][CH:14]=[C:13]2[CH2:17][CH2:18][NH2:19]

参加物

5

反応物 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 67443309HCID 67443309、化合物

生成物 1

HCID 27693627-Fluorotryptamine収率 12.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Combine lithium aluminum hydride (12.8 g; 336.1 mmol) and 0° C. anhydrous tetrahydrofuran (160 mL). Cool resulting exotherm to 0° C. Add 7-fluoro-3-(2-nitrovinyl)-1H-indole (11.55 g, 56.0 mmol) in anhydrous THF (200 mL) dropwise. After 30 min, warm to ambient temperature. After 4 hours, cool to 0° C. and add saturated sodium sulfate solution (35 mL) dropwise. Filter the solids and wash with THF and ethyl acetate. Concentrate the filtrate and dissolve the residue in methylene chloride. Filter the precipitate to give 1.26 g of product as brown crystals. Concentrate the filtrate and chromatograph on silica gel eluting with 5%, 7%, 10% 2N ammonia in methanol/methylene chloride to give product: MS (m/e): 179 (M+1), 177 (M−1); Calculated for C10H11FN2: Calcd: C, 67.40; H, 6.22; N, 15.72. Found: C, 67.06; H, 6.11; N, 15.48.

後処理

  1. temperatureCool
  2. customresulting exotherm to 0° C
  3. waitAfter 4 hours
  4. temperaturecool to 0° C.
  5. filtrationFilter the solids
  6. washwash with THF and ethyl acetate
  7. concentrationConcentrate the filtrate
  8. dissolutiondissolve the residue in methylene chloride
  9. filtrationFilter the precipitate

出典と根拠

ORDレコード
ord-fc385479db30486d87ff6596f2c150fd
出典データセット
uspto-grants-2011_10
特許番号
US08044090B2

反応ノート

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