5-Benzyloxyindole → HCID 14855720, compound

HRID 440168Notes

Reaction equation

HRID 440168 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[C:18]1[C:19]([N:21](C)[C:22](=[O:40])[C:23]=1[C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26](C(OC(C)(C)C)=O)[CH:25]=1)=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Mg]Br)C.C(OC1C=C2C(=CC=1)NC=C2)C1C=CC=CC=1.BrC1C(N(C)C(=O)C=1C1C2C(=CC=CC=2)N(C(OC(C)(C)C)=O)C=1)=O.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[C:18]1[C:19]([NH:21][C:22](=[O:40])[C:23]=1[C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 146245-BenzyloxyindoleHCID 25517Ammonium ChlorideHCID 9865966HCID 9865966, compoundHCID 14855711HCID 14855711, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 14855720HCID 14855720, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
50 °C

Procedure

The 2-(5-benzyloxy-1H-indol-3-yl)-3-(1-tert.-butoxycarbonyl-1H-indol-3-yl)-N-methylmaleinimide used as starting material is prepared as follows: A solution of 20 mmol ethyl magnesium bromide in 30 ml tetrahydrofuran is mixed with a solution of 4.46 g (20 mmol) 5-benzoxyindole in 20 ml tetrahydrofuran. The reaction mixture is maintained at 50° C. for 1 hour and then, within the course of 1 hour, a solution of 3.0 g (7.4 mmol) 2-bromo-3-[1-tert.-butoxycarbonyl-1H-indol-3-yl]-N-methylmaleinimide (Tetrahedron, 44, 2887/1988) in 40 ml tetrahydrofuran added dropwise thereto. The reaction mixture is heated under reflux for 2 hours, allowed to cool and then decomposed with a saturated aqueous solution of ammonium chloride. The reaction product is extracted with ethyl acetate, the organic phase is dried over anhydrous sodium sulphate and evaporated to dryness. The residue is flash chromatographed on silica gel (Merck Type 7734) using dichloromethane as elution agent. After elution of unreacted starting material, the desired product is obtained by evaporation of the appropriate fractions and stirring the red residue with a little toluene. There are obtained 1.3 g (32% of theory) of red crystals; m.p. 123° C.

Workup

  1. customis prepared
  2. temperatureThe reaction mixture is heated
  3. temperatureunder reflux for 2 hours
  4. temperatureto cool
  5. extractionThe reaction product is extracted with ethyl acetate
  6. dry with materialthe organic phase is dried over anhydrous sodium sulphate
  7. customevaporated to dryness
  8. customchromatographed on silica gel (Merck Type 7734)
  9. washas elution agent
  10. washAfter elution

Sources & evidence

ORD record
ord-7c243ce6d3664ca9b032d76668b0f822
Source dataset
uspto-grants-1996_05
Patent number
US05516915

Reaction notes

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