Lithium Bromide → HCID 52948638, compound

HRID 877521Notes

Reaction equation

HRID 877521 reaction equation
[CH2:1]([C:8]1(Br)[CH2:20][CH2:19][C:18]2[C:17]3[C:12](=[CH:13][C:14]([Cl:22])=[C:15]([Cl:21])[CH:16]=3)[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][C:14]([Cl:22])=[C:15]([Cl:21])[CH:16]=3)[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 67377985HCID 67377985, compound

Product 1

HCID 52948638HCID 52948638, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 2-benzyl-2-bromo-6,7-dichloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.3 g, 0.71 mmol) in anhydrous DMF (5 mL), LiBr (68 mg, 0.78 mmol) followed by Li2CO3 (52 mg, 0.71 mmol) were added. The reaction mixture was heated to 90° C. for 1 h, cooled to room temperature and diluted with water. The reaction mixture was extracted with EtOAc (3×20 mL) to obtain the crude material which was purified by silica gel chromatography [EtOAc-hexane (3:17) as eluant] to give the title compound as a light brown solid (0.07 g, 30%). 1H NMR (500 MHz, DMSO-d6, δ in ppm) 10.98 (s, 1H), 9.18 (s, 1H), 8.29 (s, 1H), 7.74 (s, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.26-7.25 (m, 4H), 7.24-7.23 (m, 1H), 6.92 (d, J=8.0 Hz, 1H), 4.11 (s, 2H).

Workup

  1. additionwere added
  2. temperaturecooled to room temperature
  3. extractionThe reaction mixture was extracted with EtOAc (3×20 mL)
  4. customto obtain the crude material which
  5. customwas purified by silica gel chromatography [EtOAc-hexane (3:17) as eluant]

Sources & evidence

ORD record
ord-ec3e3f8b8bc04092a2139538e8b22bb4
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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