Carbazole → HCID 66873619, compound

HRID 403638Notes

Reaction equation

HRID 403638 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][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][CH2:21][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)[CH3:27]

Participants

4

Reactant 3

HCID 6854CarbazoleHCID 24758Sodium hydrideHCID 122490Ethyl 7-bromoheptanoate

Product 1

HCID 66873619HCID 66873619, compoundYield 66.3%

Conditions

Temperature
50 °C

Procedure

A RB flask fitted with reflux condenser containing carbazole (0.60 g, 3.59 mmol) and sodium hydride (60 wt. % in mineral oil, 0.22 g, 5.38 mmol) was vacuum purged and filled with argon, followed by addition of DMF (16 mL). After stirring at 50° C. for 20 min, ethyl 7-bromo-heptanoate (0.85 g, 3.59 mmol) was added and the mixture stirred at 80° C. overnight. The reaction was quenched by addition of 5% aqueous NH4Cl (75 mL), transferred to a separatory funnel and extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine (2×20 L), dried (Na2SO4) and concentrated. Purification by MPCC (0-50% gradient of ethyl acetate in hexane) afforded the title compound (0.77 g, 66%). 1H NMR (300 MHz, CDCl3): δ 8.15 (d, 2H, J=7.8 Hz), 7.52 (t, 2H, J=7.3 Hz), 7.44 (d, 2H, J=8.1 Hz), 7.28 (t, 2H, J=7.7 Hz), 4.32 (t, 2H, J=7.2 Hz), 4.16 (q, 2H, J=7.1 Hz), 2.30 (t, 2H, J=7.4 Hz), 1.91 (m, 2H), 1.64 (m, 2H), 1.41 (m, 4H), 1.30 (t, 3H, J=7.2 Hz). 13C NMR APT (100 MHz, CDCl3): 173.7 (up), 140.5 (up), 125.6 (down), 122.9 (up), 120.4 (down), 118.8 (down), 108.7 (down), 60.3 (up), 43.0 (up), 34.3 (up), 28.9 (up), 27.0 (up), 24.8 (up), 14.3 (down). ESI-HRMS (m/z): [M+H]+ calcd. for C21H25NO2, 324.1958. found, 324.1957

Workup

  1. customA RB flask fitted
  2. temperaturewith reflux condenser
  3. custompurged
  4. additionfilled with argon
  5. additionfollowed by addition of DMF (16 mL)
  6. stirringthe mixture stirred at 80° C. overnight
  7. customThe reaction was quenched by addition of 5% aqueous NH4Cl (75 mL)
  8. customtransferred to a separatory funnel
  9. extractionextracted with ethyl acetate (3×30 mL)
  10. washThe combined organic layers were washed with brine (2×20 L)
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated
  13. customPurification by MPCC (0-50% gradient of ethyl acetate in hexane)

Sources & evidence

ORD record
ord-e4ff94ed8a324ada8e265dacf7458fe2
Source dataset
uspto-grants-2014_06
Patent number
US08748451B2

Reaction notes

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