Lithium Bromide → HCID 52945868, compound

HRID 877513Notes

Reaction equation

HRID 877513 reaction equation
Br[CH:2]1[CH2:14][CH2:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([C:15]#[N:16])[CH:10]=3)[NH:5][C:4]=2[C:3]1=[O:17].[Li+].[Br-]>CN(C=O)C>[OH:17][C:3]1[CH:2]=[CH:14][CH:13]=[C:12]2[C:4]=1[NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:15]#[N:16])=[CH:10][C:11]2=1

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 67378336HCID 67378336, compound

Product 1

HCID 52945868HCID 52945868, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

2-Bromo-1-oxo-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile (0.1 g, 0.5 mmol) was dissolved in DMF (5 mL) and LiBr (49 mg, 0.5 mmol) followed by Li2CO3 (42 mg, 0.5 mmol) were added. The reaction mixture was heated to 150° C. for 3 h, poured into ice cold water and extracted with EtOAc (3×30 mL). The combined organic extracts were concentrated under reduced pressure to obtain the crude compound which was purified by column chromatography [EtOAc-hexane (3:17) as eluant] to furnish the title compound as a white solid (0.04 g, 40%). 1H NMR (500 MHz, CDCl3, δ in ppm) 11.71 (s, 1H), 10.03 (s, 1H), 8.61 (s, 1H), 7.70-7.66 (m, 2H), 7.58 (d, J=8.0 Hz, 1H), 7.05 (d, J=7.5 Hz, 1H), 6.91 (d, J=7.5 Hz, 1H).

Workup

  1. additionwere added
  2. additionpoured into ice cold water
  3. extractionextracted with EtOAc (3×30 mL)
  4. concentrationThe combined organic extracts were concentrated under reduced pressure
  5. customto obtain the crude compound which
  6. customwas purified by column chromatography [EtOAc-hexane (3:17) as eluant]

Sources & evidence

ORD record
ord-b726015709af40fb8f5ff06e7c1406e8
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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