Oxindole → HCID 76684428, compound

HRID 2202643Notes

Reaction equation

HRID 2202643 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[O:11]1[CH2:13][CH:12]1[CH2:14][N:15]1[CH2:24][CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1>C(O)C>[CH2:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:23][CH2:24][N:15]1[CH2:14][CH:12]([OH:11])[CH2:13][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10]

Participants

4

Reactant 2

HCID 321710OxindoleHCID 167845312-[(Oxiran-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 76684428HCID 76684428, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of indolin-2-one (50.0 mg, 0.378 mmol) in ethanol (5 mL) was added 2-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline (85.0 mg, 0.451 mmol). The mixture was heated under microwave conditions at 120° C. for 0.5 h, concentrated and purified by preparative HPLC purification. (40.0 mg, yield 33.0%) MS (ESI+) e/z: 323.1 [M+1]+. 1H NMR (MeOD, 400 MHz), δ ppm: 7.30-7.23 (m, 2H), 7.14-7.07 (m, 4H), 7.06 (d, J=7.5 Hz, 1H), 7.01 (t, J=5.8 Hz, 1H), 4.94 (d, J=7.8 Hz, 2H), 4.31-4.18 (m, 1H), 3.97-3.86 (m, 1H), 3.82-3.72 (m, 1H), 3.71-3.64 (m, 2H), 2.90-2.73 (m, 4H), 2.73-2.59 (m, 2H).

Workup

  1. concentrationconcentrated
  2. custompurified by preparative HPLC purification

Sources & evidence

ORD record
ord-44eb600f5e054afd9702901aa2ea6b72
Source dataset
uspto-grants-2016_06
Patent number
US09365555B2

Reaction notes

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