3-ethyl-2,3-dihydro-1H-indole → HCID 19029095, compound

HRID 2255922Notes

Reaction equation

HRID 2255922 reaction equation
[CH3:1][N:2]1[C:7]([CH3:8])=[CH:6][C:5](OS(C(F)(F)F)(=O)=O)=[CH:4][C:3]1=[O:17].[CH2:18]([CH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH2:21]1)[CH3:19]>>[CH3:1][N:2]1[C:7]([CH3:8])=[CH:6][C:5]([N:22]2[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]([CH2:18][CH3:19])[CH2:21]2)=[CH:4][C:3]1=[O:17]

Participants

3

Reactant 2

HCID 5245013-ethyl-2,3-dihydro-1H-indoleHCID 19029084HCID 19029084, compound

Product 1

HCID 19029095HCID 19029095, compoundYield 62%

Conditions

Temperature
150 °C

Procedure

A mixture of 1,6-dimethyl-4-(trifluoromethanesulphonyloxy)-2-pyridone (1.5 g, 5.5 mM) and 3-ethylindoline (1.22 g, 83 mM) was heated at an external temperature of 150° C. under argon for 3 hours. The solution was cooled. The residue was triturated with acetone to afford a solid which was collected by filtration. This solid was washed with acetone to give 1,6-dimethyl-4-(3-ethylindolin-1-yl)-2-pyridone as the hemi-trifluoromethylsulphonate salt; (1.76 g, 62% yield); m.p. 174°-175° C.; microanalysis, found C, 60.2; H, 6.0: N, 8.0%; C18H21N2. 0.5CF3SO3H requires: C, 60.1; H, 5.9; N, 8.0%: NMR (DMSOd6); 0.9-1.0(3H, t, CH2CH3), 1.4-1.6(1H, m, CHEt), 1.70-1.9(1H, m, CHEt), 2.44(3H, s, CH3), 3.25-3.4(1H, m, indoline H), 3.5(3H, s, +NCH3), 3.6-3.7(1H, m, indoline H), 4.05-4.15(1H, m, indoline H), 6.2(1H, d, pyridine CH), 6.6(1H, d, pyridine CH), 6.9-7.05(1H, t, aromatic), 7.15-7.4(3H, m, aromatic).

Workup

  1. temperatureThe solution was cooled
  2. customThe residue was triturated with acetone
  3. customto afford a solid which
  4. filtrationwas collected by filtration
  5. washThis solid was washed with acetone

Sources & evidence

ORD record
ord-bfad84d45a0b4f0f9fbc7645f8c6354c
Source dataset
uspto-grants-1997_08
Patent number
US05654298

Reaction notes

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