Potassium Hydroxide → HCID 89897839, compound

HRID 1776209Notes

Reaction equation

HRID 1776209 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[C:11]([F:15])[CH:10]=[CH:9][CH:8]=3.[OH-].[K+].[CH2:18]([CH:20]1[O:22][CH2:21]1)Br>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:18][CH:20]3[CH2:21][O:22]3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[C:11]([F:15])[CH:10]=[CH:9][CH:8]=3

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 18430EpibromohydrinHCID 86702141HCID 86702141, compound

Product 1

HCID 89897839HCID 89897839, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3,5-difluoro-9H-carbazole (0.300 g, 1.5 mmol) in N,N-dimethylformamide (5 mL) at 0° C. was added 85% potassium hydroxide (0.117 g, 1.8 mmol) and the mixture was stirred for 1 hr. Epibromohydrin (0.244 mL, 3.0 mmol) was added and the mixture was slowly warmed to room temperature and stirred for 4 hrs. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (10-50% methylene chloride/hexanes) to afford the desired product as an off-white solid (0.36 g, 94%). 1H NMR (300 MHz, CDCl3) δ 7.88 (dd, 1H, J=8.7, 2.7 Hz), 7.46-7.36 (m, 2H), 7.29-7.20 (m, 2H), 6.92 (dd, 1H, J=9.9, 7.8 Hz), 4.68 (dd, 1H, J=15.9, 3.0 Hz), 4.35 (dd, 1H, J=15.9, 5.1 Hz), 3.36 (m, 1H), 2.85 (t, 1H, J=4.5 Hz), 2.56 (dd, 1H, J=4.5, 2.7 Hz).

Workup

  1. stirringstirred for 4 hrs
  2. customThe mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried (anhydrous sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (10-50% methylene chloride/hexanes)

Sources & evidence

ORD record
ord-d9599894eae1486790cfaac8ccfb1e38
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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