Triethylamine → 1H-Indolamine

HRID 966505

반응식

HRID 966505 반응식
CC([N:6]1CCCC1)(C)CO.C(N(CC)CC)C.C1(C)C(S(Cl)(=O)=O)=CC=CC=1.C[C:30]1[NH:31][C:32]2[C:37]([C:38]=1C(OCC1C=CC=CC=1)=O)=[CH:36][C:35](O)=[CH:34][CH:33]=2.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C.CO.C(N(CC)CC)C>[NH:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:38]=[C:30]1[NH2:6]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 109239755-Hydroxy-2-methyl-1H-indole-3-carboxylic acid benzyl esterHCID 223118122-Methyl-2-(pyrrolidin-1-yl)propan-1-ol

생성물 1

HCID 1220741H-Indolamine수율 5.5%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 21980445Ethyl acetate methanol triethylamine용매

실험 절차

Crude 2-methyl-2-pyrrolidin-1-yl-propan-1-ol (0.849 g, 5.94 mmol, 1 eq) was suspended in dry acetonitrile (30 mL) under Ar. Triethylamine (1.4 mL, 10 mmol, 1.7 eq) was added followed by the addition of toluenesulfonyl chloride (1.05 g, 5.50 mmol, 1.0 eq). The reaction mixture was stirred at room temperature for 1 hour. After 4 hours, the reaction was treated with 2-methyl-3-benzyloxycarbonyl-5-hydroxyindole (1.5 g; 5.5 mmol, 1 eq) and potassium carbonate (1.38 g, 10 mmol, 1.7 eq.). The reaction was heated to reflux and followed by TLC (ethyl acetate/methanol/triethylamine 87/10/3). After 23 hours, the reaction was loaded directly on silica gel and chromatographed (ethyl acetate/methanol/triethylamine 87/10/3). Impure product was further purified by reverse-phase prep-HPLC 10-100% Acetonitrile/water, 0.1% TFA. 0.040 g (5% yield) of the indole-amine was obtained as a brown semisolid: LC/MS (ESI+) 407 (M+1), Anal. (C24H30N2O2.TFA.1.0H2O) C, H, N.

후처리

  1. waitAfter 4 hours
  2. temperatureThe reaction was heated
  3. temperatureto reflux
  4. waitAfter 23 hours
  5. customchromatographed (ethyl acetate/methanol/triethylamine 87/10/3)
  6. customImpure product was further purified by reverse-phase prep-HPLC 10-100% Acetonitrile/water, 0.1% TFA

출처 및 근거

ORD 기록
ord-e75ea8e849854a179a962faf161b13e7
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951848B2

연결된 노트

불러오는 중…