Trifluoroacetic acid → 1-Ethyl-3-hydroxy-3-((3-methoxypyridin-2-yl)methyl)-5-methylindolin-2-one

HRID 1523053노트

반응식

HRID 1523053 반응식
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[C:5](=[O:13])[C:4]1=[O:14])[CH3:2].[CH3:15][O:16][C:17]1[C:18]([CH3:23])=[N:19][CH:20]=[CH:21][CH:22]=1.FC(F)(F)C(O)=O>O1CCOCC1>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[C:5]([OH:13])([CH2:23][C:18]2[C:17]([O:16][CH3:15])=[CH:22][CH:21]=[CH:20][N:19]=2)[C:4]1=[O:14])[CH3:2]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 24713051-ethyl-5-methyl-2,3-dihydro-1H-indole-2,3-dioneHCID 30152703-Methoxy-2-methylpyridine

생성물 1

HCID 863003991-Ethyl-3-hydroxy-3-((3-methoxypyridin-2-yl)methyl)-5-methylindolin-2-one

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
110 °C

실험 절차

To a flame dried sealed tube cooled under argon was added the 1-ethyl-5-methylindoline-2,3-dione (0.03 grams, 0.15 mmol) and 3-methoxy-2-methyl-pyridine (0.072 grams, 0.59 mmol, purchased from Fisher Scientific) and 0.5 mL of 1,4 dioxane. After the addition of trifluoro acetic acid (2 μL) the vessel was sealed and heated to 110° C. for 48 hours. The reaction was then concentrated. 1H-NMR δ 8.21 (s, 1H), 7.35 (bs, OH), 7.26 (m, 1H), 7.20 (d, 1H), 7.09 (d, 1H), 6.90 (s, 1H), 6.75 (d, 1H), 3.78 (s, 3H), 3.77 (m, 2H), 3.34 (d, 1H), 3.18 (d, 1H), 2.27 (s, 3H), 1.28 (t, 3H). Calculated mass for C18H20N2O3, 312.15. Observed 313.1 (M+1).

후처리

  1. customTo a flame dried
  2. customsealed tube
  3. temperaturecooled under argon
  4. customwas sealed
  5. concentrationThe reaction was then concentrated

출처 및 근거

ORD 기록
ord-be035068f5c04a0195ae069178012af1
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079853B2

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