Morpholine → HCID 59426387, compound

HRID 907161Notes

Reaction equation

HRID 907161 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH2:24][CH3:25])[C:13]3[C:18]([C:19]=2[C:20]#[N:21])=[CH:17][CH:16]=[C:15]([O:22][CH3:23])[CH:14]=3)=[CH:7][CH:6]=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C(#N)C>[CH2:24]([N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([O:22][CH3:23])[CH:14]=2)[C:19]([C:20]#[N:21])=[C:11]1[C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[CH:6][CH:7]=1)[CH3:25]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 59425563HCID 59425563, compound

Product 1

HCID 59426387HCID 59426387, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

2-[4-(2-bromoethoxy)-phenyl]-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (40 mg, 0.1 mmol), prepared as in step A above, was combined with morpholine (50 μL, 0.58 mmol) and acetonitrile (1.0 mL). This was heated at 85° C. for 2 h. The reaction mixture was then partitioned between CH2Cl2 and H2O. The organic layer was dried and concentrated. Purification by silica gel chromatography (6/4, acetone/hexanes) yielded 1-ethyl-6-methoxy-2-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-1H-indole-3-carbonitrile (39 mg, 96%) as a white solid.

Workup

  1. customThe reaction mixture was then partitioned between CH2Cl2 and H2O
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (6/4, acetone/hexanes)

Sources & evidence

ORD record
ord-d67fce74fb5546feab89e3f57c4afc98
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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