Potassium Iodide → HCID 21892125, compound

HRID 720427Notes

Reaction equation

HRID 720427 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2].[I-].[K+].B(Br)(Br)Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 25134Boron tribromideHCID 10245823HCID 10245823, compound

Product 1

HCID 21892125HCID 21892125, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-cyano-1-(3-methoxybenzoyl)-pyrrolo[1,2-a]quinoline (326 mg, 1 mmol), tetrabutylammonium bromide (967 mg, 3 mmol), potassium iodide (498 mg, 3 mmol), boron tribromide (1N solution in dichloromethane, 3 ml) in dichloromethane (5 ml) was refluxed for 8 h. It was cooled to room temperature and quenched with water (20 mL), the organic layer was washed with aqueous sodium bicarbonate (2×10 mL), water (2×20 mL), dried over Na2SO4, and concentrated. The residue was purified by column chromatography to give 188 mg (60%) of title compound. 1H NMR (CDCl3): 8.06 (d, J=9.0 Hz, 1H), 7.85 (d, J=7.80 Hz, 1H), 7.74–7.40 (m, 8H), 7.20–7.14 (m, 1H), 5.15 (s, 1H).

Workup

  1. temperaturewas refluxed for 8 h
  2. customquenched with water (20 mL)
  3. washthe organic layer was washed with aqueous sodium bicarbonate (2×10 mL), water (2×20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-80ea1595627f4338bb371bb40a72e567
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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