Benzyl Bromide → HCID 13383905, compound

HRID 1619475Notes

Reaction equation

HRID 1619475 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:2]=1.[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N1C2C=NC(C(OC)=O)=CC=2C2C1=CC=CC=2)C1C=CC=CC=1>C1COCC1.CN(C=O)C>[CH2:21]([N:12]1[C:13]2[CH:1]=[N:2][C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 105078Ethyl Beta-Carboline-3-CarboxylateHCID 11404295HCID 11404295, compound

Product 1

HCID 13383905HCID 13383905, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl β-carboline-3-carboxylate 10 (4.8 g, 20 mmol), DMF (100 ml) and THF (100 ml) were respectively added in a 100 ml round-bottom flask, and were stirred at room temperature for 15 minutes, then 60% NaH (2.4 g, 60 mmol) was added and stirred until there were no bubbles formed. Benzyl bromide (15 ml) was added, and the mixture was refluxed for 12 h. Later the mixture was treated in a manner similar to that described for compound 29 to afford white crystals (4.6 g, 70%), mp 126-127° C.

Workup

  1. stirringstirred until there
  2. customformed
  3. temperaturethe mixture was refluxed for 12 h
  4. additionLater the mixture was treated in a manner similar to

Sources & evidence

ORD record
ord-530e5aaac78a4cd8a12a7adae92b7627
Source dataset
uspto-grants-2014_07
Patent number
US08772311B2

Reaction notes

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