Iodine → HCID 59640834, compound

HRID 549216Notes

Reaction equation

HRID 549216 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:19]([F:20])=[C:18](Cl)[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[N:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.C([Li])CCC.[I:27]I>O1CCCC1.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:19]([F:20])=[C:18]([I:27])[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[N:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 807IodineHCID 59640848HCID 59640848, compoundHCID 178418339Butyllithium

Product 1

HCID 59640834HCID 59640834, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a −78° C. solution of 2-benzo[1,3]dioxol-5-yl-4-chloro-3-fluoro-quinoline (from step A, 0.073 g, 0.24 mmol) in tetrahydrofuran (2 mL) was added butyl lithium (0.36 mL, 2.5 M in hexane, 0.6 mmol). The resulting reaction mixture was stirred for 3 h., after which a solution of iodine (0.06 g, 0.24 mmol) in 0.8 mL of THF was added. The reaction mixture was stirred for an additional 2 h. and diluted with water (20 mL). The aqueous layer was extracted with ethyl acetate (2×25 mL). The combined organic layers were dried over sodium sulfate, concentrated and purified via silica gel column chromatography to give the title compound (0.046 g, 48%). MS (ES) 393.8 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. stirringThe reaction mixture was stirred for an additional 2 h.
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×25 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified via silica gel column chromatography

Sources & evidence

ORD record
ord-e36708798ef34f3c99aa3cce72aac903
Source dataset
uspto-grants-2011_05
Patent number
US07943640B2

Reaction notes

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