Carbazole → HCID 66873467, compound

HRID 403625Notes

Reaction equation

HRID 403625 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+].[CH2:16]([O:18][C:19](=[O:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br)[CH3:17]>CN(C=O)C.[I-].[K+]>[CH2:16]([O:18][C:19](=[O:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][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)[CH3:17]

Participants

6

Reactant 3

HCID 6854CarbazoleHCID 24758Sodium hydrideHCID 117544Ethyl 6-bromohexanoate

Product 1

HCID 66873467HCID 66873467, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Carbazole (2.0 g, 12.0 mmol) and sodium hydride (60 wt. % in mineral oil, 0.29 g, 12.0 mmol) were placed under argon and dissolved in DMF (5 mL). After stirring for 30 minutes, 6-bromo-hexanoic acid ethyl ester (2.0 mL, 12.0 mmol) and potassium iodide (10 mg) were added to the reaction. The reaction was heated to 80° C. for 2 h. The reaction was then quenched with water (30 mL) followed by addition of ethyl acetate (30 mL). The organic layer was isolated and the aqueous layer extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with water (2×20 mL), brine (15 mL), dried (Na2SO4) and concentrated in vacuo. Purification by column chromatography (0-80% gradient of ethyl acetate in hexane) afforded the title compound (2.7 g, 73%) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 8.13 (d, 2H, J=7.7 Hz), 7.56 (d, 2H, J=8.2 Hz), 7.42 (m, 2H), 7.26 (m, 2H), 4.34 (t, 2H, J=7.0 Hz), 4.13 (q, 2H, J=7.1 H), 2.29 (t, 2H, J=7.3 Hz), 1.93 (m, 2H), 1.70 (m, 2H), 1.45 (m, 2H), 1.25 (t, 3H, J=7.1 Hz). 13C NMR (100 MHz, DMSO): δ 173.1, 140.4, 126.1, 122.5, 120.7, 119.0, 109.6, 60.0, 42.5, 33.8, 28.7, 26.4, 24.7, 14.5. ESI-HRMS (m/z): [M+H]+ calcd. for C20H23NO2, 310.1802. found, 310.1792.

Workup

  1. customThe reaction was then quenched with water (30 mL)
  2. additionfollowed by addition of ethyl acetate (30 mL)
  3. customThe organic layer was isolated
  4. extractionthe aqueous layer extracted with ethyl acetate (2×10 mL)
  5. washThe combined organic layers were washed with water (2×20 mL), brine (15 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customPurification by column chromatography (0-80% gradient of ethyl acetate in hexane)

Sources & evidence

ORD record
ord-83ae763e7eb2415f8823ac73f7451ddd
Source dataset
uspto-grants-2014_06
Patent number
US08748451B2

Reaction notes

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