Carbazole → HCID 54249395, compound

HRID 1420705Notes

Reaction equation

HRID 1420705 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]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:17][C@H:18]([CH3:21])[CH2:19][OH:20]>CN(C=O)C>[CH:10]1[C:11]2[N:12]([CH2:17][C@@H:18]([CH3:21])[CH2:19][OH:20])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6854CarbazoleHCID 24758Sodium hydrideHCID 10441885(R)-(-)-3-Bromo-2-methyl-1-propanol

Product 1

HCID 54249395HCID 54249395, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

Carbazole (0.50 g, 3.0 mmol) was dissolved in dry DMF (20 mL) and NaH (60% dispersion in oil) (0.36 g, 9.0 mmol) was added. The resulting mixture was stirred under a N2 atmosphere at 25° C. for 30 min. (R)-(-)-3-Bromo-2-methyl-1-propanol (1.14 g, 7.5 mmol) was added in 4 portions over a period of 10 min, and the mixture stirred at 45° C. for 48 h. The solvent was removed in vacuo. Addition of water (20 mL), extraction with CH2Cl2 (3×20 ml), drying of the organic phases (MgSO4) and evaporation of the solvent in vacuo gave an oil that was purified on a silica gel column (Eluent: ethyl acetate/n-heptane (1:1)). This afforded the title compound 0.16 g (23%) as a white solid. M.p. 80-81° C.

Workup

  1. additionwas added in 4 portions over a period of 10 min
  2. customThe solvent was removed in vacuo
  3. additionAddition of water (20 mL), extraction with CH2Cl2 (3×20 ml)
  4. dry with materialdrying of the organic phases (MgSO4) and evaporation of the solvent in vacuo
  5. customgave an oil that
  6. customwas purified on a silica gel column (Eluent: ethyl acetate/n-heptane (1:1))

Sources & evidence

ORD record
ord-74774eed79f9444ebfa96b1b69a1e02e
Source dataset
uspto-grants-2000_06
Patent number
US06071932

Reaction notes

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