1,2-Dichloroethane → HCID 59430657, compound

HRID 907181Notes

Reaction equation

HRID 907181 reaction equation
BrC[C:3]1([O:25][CH3:26])[CH:11]=[C:10]2[C:6](=[C:7]([C:23]#[N:24])[CH:8]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)[N:9]2[CH2:12][CH3:13])[CH:5]=[CH:4]1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.Cl[CH2:34]CCl>>[CH2:12]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([CH2:34][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[C:3]([O:25][CH3:26])[CH:11]=2)[C:7]([C:23]#[N:24])=[C:8]1[C:14]1[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=1)[CH3:13]

Participants

4

Reactant 3

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 66865671HCID 66865671, compound

Product 1

HCID 59430657HCID 59430657, compoundYield 44%

Procedure

Crude 6-bromomethyl-1-ethyl-6-methoxy-2-(4-nitro-phenyl)-1H-indole-3-carbonitrile (0.3 mmol) was heated with morpholine (150 μL, 1.75 mmol) and DCE (1.0 mL) at 90° C. overnight. The reaction mixture was then partitioned between H2O and EtOAc. The organic layer was dried and concentrated. Purification by silica gel chromatography (50-100%, EtOAc/CH2Cl2), followed by trituration with 1/1 hexane/acetone yielded 1-ethyl-6-methoxy-5-morpholin-4-ylmethyl-2-(4-nitrophenyl)-1H-indole-3-carbonitrile (57 mg, 44% overall yield) as a yellow solid.

Workup

  1. customThe reaction mixture was then partitioned between H2O and EtOAc
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (50-100%, EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-edd7e8c4f0cc428491139274609320cc
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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