Lithium Bromide → HCID 52947094, compound

HRID 877514Notes

Reaction equation

HRID 877514 reaction equation
Br[CH:2]1[CH2:14][CH2:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([Cl:16])[C:10]=3[Cl:15])[NH:5][C:4]=2[C:3]1=[O:17].[Li+].[Br-]>CN(C=O)C>[Cl:15][C:10]1[C:9]([Cl:16])=[CH:8][CH:7]=[C:6]2[C:11]=1[C:12]1[CH:13]=[CH:14][CH:2]=[C:3]([OH:17])[C:4]=1[NH:5]2

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 67377903HCID 67377903, compound

Product 1

HCID 52947094HCID 52947094, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

2-Bromo-5,6-dichloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.1 g, 0.33 mmol) was dissolved in anhydrous DMF (4 mL) and LiBr (0.031 g, 0.35 mmol) followed by Li2CO3 (26 mg, 0.35 mmol) were added. The reaction mixture was heated to 150° C. for 30 min, then cooled to room temperature, poured into ice water and extracted with EtOAc (3×20 mL). The combined organic extracts were concentrated in vacuo to obtain the crude compound which was purified by column chromatography [EtOAc-hexane (1:9) as eluant] to give the title compound as an ash solid (0.04 g, 40%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.38 (bs, 1H), 8.20 (d, J=9.0 Hz, 1H), 7.48 (d, J=8.5 Hz, 1H), 7.33 (d, J=9.0 Hz, 1H), 7.16 (m, 1H), 6.91 (d, J=8.0 Hz, 1H), 5.10 (bs, 1H).

Workup

  1. additionwere added
  2. temperaturecooled to room temperature
  3. extractionextracted with EtOAc (3×20 mL)
  4. concentrationThe combined organic extracts were concentrated in vacuo
  5. customto obtain the crude compound which
  6. customwas purified by column chromatography [EtOAc-hexane (1:9) as eluant]

Sources & evidence

ORD record
ord-61ad50b588644cfea1a8af2631a768bf
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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