Lithium Bromide → HCID 52942225, compound

HRID 877512Notes

Reaction equation

HRID 877512 reaction equation
Br[CH:2]1[CH2:14][CH2:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([Br:15])[CH:10]=3)[NH:5][C:4]=2[C:3]1=[O:16].[Li+].[Br-]>CN(C=O)C>[Br:15][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4]1[C:3]([OH:16])=[CH:2][CH:14]=[CH:13][C:12]2=1

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 67378014HCID 67378014, compound

Product 1

HCID 52942225HCID 52942225, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2,6-dibromo-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.35 g, 1.02 mmol) in anhydrous DMF (10 mL), LiBr (0.097 g, 1.11 mmol) followed by Li2CO3 (0.082 g, 1.11 mmol) were added and the resulting mixture was heated at 150° C. for 4 h. The reaction mixture was poured into ice cold water and extracted with EtOAc (2×20 mL). The combined organic extracts were dried over Na2SO4, concentrated in vacuo and purified by column chromatography [EtOAc/hexane (3:17) as eluant] to give the title compound as a brown-colored solid (0.180 g, 69%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.23 (bs, 1H), 8.17 (s, 1H), 7.61 (d, J=8.0 Hz, 1H), 7.50 (d, J=8.5 Hz, 1H), 7.32 (d, J=9.5 Hz, 1H), 7.08 (m, 1H), 6.80 (d, J=7.5 Hz, 1H), 5.01 (bs, 1H).

Workup

  1. additionwere added
  2. additionThe reaction mixture was poured into ice cold water
  3. extractionextracted with EtOAc (2×20 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography [EtOAc/hexane (3:17) as eluant]

Sources & evidence

ORD record
ord-9aed40545bd64388adf36e99d1de4b76
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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