Carbazole → HCID 66873067, compound

HRID 403637Notes

Reaction equation

HRID 403637 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][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24]C)=[O:22]>CN(C=O)C>[CH3:24][O:23][C:21](=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2

Participants

5

Reactant 3

HCID 6854CarbazoleHCID 24758Sodium hydrideHCID 84580Ethyl 5-bromovalerate

Product 1

HCID 66873067HCID 66873067, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a round bottom flask fitted with reflux condenser containing carbazole (1.00 g, 5.98 mmol) and sodium hydride (60 wt. % in mineral oil, 0.29 g, 7.18 mmol), was added DMF (22 mL). After stirring at 50° C. for 20 min, ethyl 5-bromopentanoate (0.95 mL, 5.98 mmol) was added and the mixture stirred at 80° C. overnight. The reaction was quenched by addition of 5% aqueous NH4Cl (100 mL), transferred to a separatory funnel and extracted with ethyl acetate (3×40 mL). The combined organic layers were washed with brine (2×20 mL), dried (Na2SO4) and concentrated. Purification by MPCC (0-40% gradient of ethyl acetate in hexane) afforded the title compound (0.87 g, 49%). 1H NMR (400 MHz, CDCl3): δ 8.14 (d, 2H, J=7.8 Hz), 7.51 (t, 2H, J=7.2 Hz), 7.43 (d, 2H, J=8.2 Hz), 7.27 (t, 2H, J=7.4 Hz), 4.35 (t, 2H, J=7.1 Hz), 4.13 (q, 2H, J=7.1 Hz), 2.35 (t, 2H, J=7.3 Hz), 1.98-1.91 (m, 2H), 1.79-1.72 (m, 2H), 1.25 (t, 3H, J=7.1 Hz). 13C NMR APT (100 MHz, CHCl3): δ 173.2 (up), 140.3 (up), 125.6 (down), 122.89 (up), 120.4 (down), 118.9 (down), 108.6 (down), 60.4 (up), 42.7 (up), 33.9 (up), 28.4 (up), 22.7 (up), 14.2 (down). ESI-HRMS (m/z): [M+H]+ calcd. for C19H21NO2, 296.1645. found, 296.1650.

Workup

  1. customTo a round bottom flask fitted
  2. temperaturewith reflux condenser
  3. stirringthe mixture stirred at 80° C. overnight
  4. customThe reaction was quenched by addition of 5% aqueous NH4Cl (100 mL)
  5. customtransferred to a separatory funnel
  6. extractionextracted with ethyl acetate (3×40 mL)
  7. washThe combined organic layers were washed with brine (2×20 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customPurification by MPCC (0-40% gradient of ethyl acetate in hexane)

Sources & evidence

ORD record
ord-07f9779f0421410b950dd446ce70fb0a
Source dataset
uspto-grants-2014_06
Patent number
US08748451B2

Reaction notes

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