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

HRID 1523053Notes

Reaction equation

HRID 1523053 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-be035068f5c04a0195ae069178012af1
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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