Carbazole → HCID 66873124, compound

HRID 403639Notes

Reaction equation

HRID 403639 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+].[CH3:16][O:17][C:18](=[O:28])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26]Br)=[CH:22][CH:21]=1>CN(C=O)C.C(OCC)(=O)C.O.[I-].[K+]>[CH3:16][O:17][C:18](=[O:28])[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[CH:24][CH:25]=1

Participants

8

Reactant 3

HCID 6854CarbazoleHCID 24758Sodium hydrideHCID 11770640Methyl 2-(4-(bromomethyl)phenyl)acetate

Product 1

HCID 66873124HCID 66873124, compoundYield 36%

Reagents, catalysts & solvents 4

HCID 4875Potassium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Carbazole (1.0 g, 6.0 mmol) and sodium hydride (60 wt. % in mineral oil, 0.14 g, 6.0 mmol) were placed under argon and dissolved in DMF (5 mL). The mixture was stirred at room temperature for 30 min, followed by treatment with (4-bromomethylphenyl)acetic acid methyl ester (1.5 g, 6.0 mmol) and 5 mg of potassium iodide. The reaction was heated to 80° C. for 2 h. The reaction was then diluted with ethyl acetate (30 mL) and water (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 (0.71 g, 36%) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 8.20 (d, 2H, J=7.7 Hz), 7.49 (m, 2H), 7.40 (d, 2H, J=8.1 Hz), 7.32 (m, 2H), 7.17 (d, 2H, J=8.1 Hz), 7.12 (d, 2H, J=8.1 Hz), 5.52 (s, 2H), 3.71 (s, 3H), 3.61 (s, 2H). 13C NMR (100 MHz, CDCl3): δ 171.6, 140.3, 135.7, 132.8, 129.3, 126.5, 125.5, 122.8, 120.1, 118.9, 108.5, 51.7, 45.9, 40.4. ESI-HRMS (m/z): [M+H]+ calcd. for C22H19NO2, 330.1489. found, 330.1494.

Workup

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

Sources & evidence

ORD record
ord-cf3d0821c624443b971629d72f783c95
Source dataset
uspto-grants-2014_06
Patent number
US08748451B2

Reaction notes

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