Lithium Bromide → HCID 52941376, compound

HRID 877518Notes

Reaction equation

HRID 877518 reaction equation
[CH2:1]([C:8]1(Br)[CH2:20][CH2:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Cl:22])[C:16]=3[Cl:21])[NH:11][C:10]=2[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[Br-]>CN(C=O)C.O>[CH2:1]([C:8]1[CH:20]=[CH:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Cl:22])[C:16]=3[Cl:21])[NH:11][C:10]=2[C:9]=1[OH:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 82050Lithium BromideHCID 67378055HCID 67378055, compound

Product 1

HCID 52941376HCID 52941376, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2-Benzyl-2-bromo-5,6-dichloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.48 g, 1.14 mmol) was dissolved in DMF (4 mL) and LiBr (0.1 g, 1.25 mmol) followed by Li2CO3 (0.09 g, 1.25 mmol) were added. The reaction mixture was heated to 90° C. for 1 h, then cooled to room temperature, diluted with water and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the crude compound which was purified by column chromatography [EtOAc-hexane (3:17) as eluant] to provide the title compound as a light green solid (0.215 g, 56%). 1H NMR (500 MHz, DMSO-d6, δ in ppm) 11.31 (s, 1H), 9.22 (s, 1H), 7.88 (d, J=8.5 Hz, 1H), 7.52 (s, 2H), 7.26-7.23 (m, 4H), 7.18-7.20 (m, 1H), 6.97 (d, J=8.0 Hz, 1H), 4.14 (s, 2H).

Workup

  1. additionwere added
  2. temperaturecooled to room temperature
  3. extractionextracted with EtOAc (3×20 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give the crude compound which
  7. customwas purified by column chromatography [EtOAc-hexane (3:17) as eluant]

Sources & evidence

ORD record
ord-e68e6531a98941a6b316acebaae65bae
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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