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Dimethylamine → 3-(2-(1H-indol-3-yl)-2-oxoethyl)-1-(3-azidopropyl)-3-hydroxy-5-methylindolin-2-one

HRID 1523072
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HRID 1523072 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=[O:12])[CH3:11])=[CH:2]1.[N:13]([CH2:16][CH2:17][CH2:18][N:19]1[C:27]2[C:22](=[CH:23][C:24]([CH3:28])=[CH:25][CH:26]=2)[C:21](=[O:29])[C:20]1=[O:30])=[N+:14]=[N-:15].CNC>CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=[O:12])[CH2:11][C:21]2([OH:29])[C:22]3[C:27](=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=3)[N:19]([CH2:18][CH2:17][CH2:16][N:13]=[N+:14]=[N-:15])[C:20]2=[O:30])=[CH:2]1
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참가 물질

5

반응물 3

HCID 674DimethylamineHCID 128023-AcetylindoleHCID 715407891-(3-Azidopropyl)-5-methylindoline-2,3-dione

생성물 1

HCID 863008283-(2-(1H-indol-3-yl)-2-oxoethyl)-1-(3-azidopropyl)-3-hydroxy-5-methylindolin-2-one

시약·촉매·용매 1

HCID 887Methanol용매

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온도
130 °C

실험 절차

To a clean Biotage microwave vial was added 1-(1H-indol-3-yl)ethanone (0.023 grams, 0.143 mmol, purchased from Fisher Scientific), 1-(3-azidopropyl)-5-methylindoline-2,3-dione (0.02 grams, 0.082 mmol) and 0.27 mL of methanol. After the addition of 9.0 μL of dimethyl amine (40% by weight solution in water, purchased from Fisher Scientific), the vial was sealed and heated in a Biotage Initiator for ten minutes at 130° C. It was then concentrated and purified using a Teledyne ISCO hexanes/ethyl acetate gradient on silica gel. A subsequent purification was done using a preparative thin layer chromatography (ethyl acetate, hexanes (2:1)). Yield 14%. 1H-NMR δ 8.87 (bs, 1H), 8.34 (m, 1H), 7.76 (s, 1H), 7.40 (m, 1H), 7.29 (m, 3H), 7.10 (d, 1H), 6.77 (d, 1H), 5.0 (bs, OH), 3.77 (m, 2H), 3.60 (d, 1H), 3.41 (t, 2H), 3.34 (d, 1H), 2.27 (s, 3H), 1.96 (m, 2H).

후처리

  1. customthe vial was sealed
  2. concentrationIt was then concentrated
  3. custompurified
  4. customA subsequent purification

출처 및 근거

ORD 기록
ord-8e1d3c418e784e2db91d354b8c5a57b7
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09079853B2

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