Ammonia → HCID 57934220, compound

HRID 1433888Notes

Reaction equation

HRID 1433888 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[C:7]([O:24]C)[CH:8]=[CH:9][C:10]=2[CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22]C)[CH:18]=3)[CH2:13]2)[C:5](=O)[C:4]1=O)[CH3:2].B.O1CCCC1.N>O1CCCC1>[CH2:1]([N:3]1[C:11]2[C:10]([CH:12]3[CH2:21][CH2:20][C:19]4[C:14](=[CH:15][CH:16]=[C:17]([OH:22])[CH:18]=4)[CH2:13]3)=[CH:9][CH:8]=[C:7]([OH:24])[C:6]=2[CH:5]=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 2723981Borane;tetrahydrofuranHCID 23087569HCID 23087569, compound

Product 1

HCID 57934220HCID 57934220, compoundYield 5.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-ethyl-4-methoxy-7-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-1H-indole-2,3-dione (160 mg), borane-tetrahydrofuran complex (1.0 M solution in tetrahydrofuran) (1.8 ml) and tetrahydrofuran (10 ml) was refluxed for 1 hour. After dilution with ice water, ammonia solution was added thereto, the solution was extracted with ethyl acetate, then washed with brine, dried over magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system), the resulting 1-ethyl-4-methoxy-7-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-1H-indole (58 mg) was used according to an analogous synthetic method to Example 364 described below to provide the title compound (7 mg).

Workup

  1. temperaturewas refluxed for 1 hour
  2. extractionthe solution was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-7e35d0214b7544c885fc98e8110af932
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

Loading…