Sodium Iodide → HCID 67273201, compound

HRID 1020911Notes

Reaction equation

HRID 1020911 reaction equation
[C:1]1([C:6]2[NH:7][C:8]3[CH:9]=[CH:10][CH:11]=[C:12]([OH:15])[C:13]=3[CH:14]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.[Na+].[I-]>CC#N>[C:1]1([C:6]2[NH:7][C:8]3[C:13]([CH:14]=2)=[C:12]([O:15][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH:11]=[CH:10][CH:9]=3)[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 67273711HCID 67273711, compound

Product 1

HCID 67273201HCID 67273201, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To 100 mg (0.503 mmol) of the intermediate 2-cyclopent-1-enyl-1H-indol-4-ol in 2 mL CH3CN was added 819 mg (2.51 mmol, 5 eq) cesium carbonate, 94 mg (0.503 mmol) of 4-(2-chloroethyl)morpholine hydrochloride and a catalytic amount of NaI. The reaction mixture was heated at 50° C. for 3 h, partitioned between EtOAc and H2O, washed with aqueous NaCl solution, dried (MgSO4), and concentrated under vacuum to yield 81 mg (52%) of 2-cyclopent-1-enyl-4-(2-morpholin-4-yl-ethoxy)-1H-indole.

Workup

  1. custompartitioned between EtOAc and H2O
  2. washwashed with aqueous NaCl solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d91dc0a29e784646bac82a0bc482ffb9
Source dataset
uspto-grants-2014_05
Patent number
US08716493B2

Reaction notes

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