Iodine → HCID 11566815, compound

HRID 2249870Notes

Reaction equation

HRID 2249870 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[C:3]=1[F:19].C([Li])CCC.[I:25]I>O1CCCC1.O>[F:19][C:3]1[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[N:5][C:6]2[C:11]([C:2]=1[I:25])=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

6

Reactant 3

HCID 807IodineHCID 11579971HCID 11579971, compoundHCID 178418339Butyllithium

Product 1

HCID 11566815HCID 11566815, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-chloro-3-fluoro-2-(2-fluoro-phenyl)-quinoline (from step E, 0.160 g, 0.47 mmol) in tetrahydrofuran (3 mL) at −78° C. was added butyl lithium (0.6 mL, 2.5 M in hexane, 1.3 mmol). The mixture was stirred for 3 h. and iodine (0.148 g, 0.58 mmol) in 0.8 mL of THF was added. The reaction mixture was stirred for an additional 2 h. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (2×25 mL). The organic layers were combined, dried over sodium sulfate, concentrated and purified by silica gel column chromatography to yield the title compound (0.148 g, 84%). MS (ES) 368.1 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred for an additional 2 h
  2. extractionextracted with ethyl acetate (2×25 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-543d02b95dc4440b9e4625fc49f21d00
Source dataset
uspto-grants-2008_01
Patent number
US07314939B2

Reaction notes

Loading…