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

HRID 229846

반응식

HRID 229846 반응식
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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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]methylamine (67% yield).

후처리

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

출처 및 근거

ORD 기록
ord-b456a65a718c4ffea822d08d3e083a9a
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563908B2

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