Trifluoroacetic acid → HCID 21249906、化合物

HRID 1532371ノート

反応式

HRID 1532371 の反応式
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=2)[NH:13][C:12]=1[C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][CH2:38][CH2:39][CH:40]=O)[CH:32]=1.FC(F)(F)C(O)=O.C([BH3-])#N.[Na+]>CO>[CH2:1]([N:8]([CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=2)[NH:13][C:12]=1[C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=1)[CH2:40][CH2:39][CH2:38][CH2:37][C:33]1[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 5003444Sodium cyanoborohydrideHCID 110190264-pyridin-3-ylbutanalHCID 21249905HCID 21249905、化合物

生成物 1

HCID 21249906HCID 21249906、化合物収率 72.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of benzyl-{2-[2-(3,5-dimethylphenyl)-5-nitro-1H-indol-3-yl]ethyl}amine (700 mg) and 4-pyridin-3-yl butyraldehyde (314 mg) were solvated in 30 mL dry methanol to which ca. 2 g powdered 3 Å molecular sieves were added. The pH of this mixture was adjusted to 5 by the addition of trifluoroacetic acid and then 441 mg sodium cyanoborohydride was added and the mixture atirred at room temperature. After 48 hours, the mixture was filtered through diatomaceous earth, concentrated in vacuo and purified by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 96:4:0; then 96:4:1) to give the title compound (676 mg).

後処理

  1. additionwere added
  2. customatirred at room temperature
  3. filtrationthe mixture was filtered through diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography on silica gel (methylene chloride

出典と根拠

ORDレコード
ord-dc9f66f7fe9b4c378086a5e05ea9c90d
出典データセット
uspto-grants-2001_03
特許番号
US06200957B1

反応ノート

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