Indole → [2-(1H-Indol-3-ylsulfanyl)benzyl]methylamine

HRID 16639

反応式

HRID 16639 の反応式
CN1[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[S:3]1.[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1.ClC(Cl)(Cl)C(O)=O.[OH-].[Na+].C(OCC)(=O)C.CO.[CH2:37]([N:39](CC)CC)C>C1COCC1.C(OCC)(=O)C>[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[CH2:6][CH2:37][NH2:39])=[CH:12]1

参加物

8

反応物 5

HCID 798IndoleHCID 6421Trichloroacetic AcidHCID 14798Sodium HydroxideHCID 124288082-Methyl-2,3-dihydro-benzo[d]isothiazoleHCID 21980445Ethyl acetate methanol triethylamine

生成物 1

HCID 15979848[2-(1H-Indol-3-ylsulfanyl)benzyl]methylamine収率 67%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-Methyl-2,3-dihydro-benzoisothiazole (VI) (Hoffmann, R. W.; Goldman, S. Chem. Ber. 111, 1978, 2716-2725) (75 mg, 0.50 mmol) was dissolved in THF (1 mL) and added to indole (V) (140 mg, 0.60 mmol) under Ar. Tricloroacetic acid (90 mg, 0.55 mmol) was added and the reaction mixture was stirred at room temperature for 16 hours. 2 mL 1N NaOH (aq) was added. Extraction with ethyl acetate (2×10 mL) and purification by flash chromatography on silica gel (eluent: ethyl acetate then ethyl acetate/methanol/triethylamine) gave 88 mg [2-(1H-Indol-3-ylsulfanyl)benzyl]methyl amine (67% yield).

後処理

  1. extractionExtraction
  2. customwith ethyl acetate (2×10 mL) and purification by flash chromatography on silica gel (eluent

出典と根拠

ORDレコード
ord-0cd3f9556eae4f608e13a494bc211cd1
出典データセット
uspto-grants-2010_06
特許番号
US07737171B2

関連ノート

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