1-Butanol → HCID 11579971, compound

HRID 549212Notes

Reaction equation

HRID 549212 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4](I)[C:3]=1[F:13].C(O)CCC.C(=O)([O-])[O-].[Cs+].[Cs+].[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[F:25])[C:3]=1[F:13]

Participants

7

Reactant 4

HCID 2631-ButanolHCID 10796Cesium carbonateHCID 27343542-Fluorophenylboronic acidHCID 59640842HCID 59640842, compound

Product 1

HCID 11579971HCID 11579971, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-chloro-3-fluoro-2-iodo-quinoline (from step D, 0.3 g, 0.9 mmol) in toluene (5 mL) was added n-butanol (2 mL), water (3 mL) and cesium carbonate (1.14 g, 3.5 mmol). The resulting mixture was degassed for 5 min. and tetrakis(triphenyl-phosphine)palladium(0) (5 mg, 5 mol %) and 2-fluorophenyl boronic acid (0.286 g, 2 mmol) were added. The reaction mixture was heated to 50° C. for 24 h., after which it was extracted with ethyl acetate. The organic layer was dried and concentrated in a rotary evaporator. The residue was purified by silica gel column chromatography using ethyl acetate/hexane gradient to yield the title compound (0.160 g, 48%). MS (ES) 336.1 (M+H)+.

Workup

  1. customThe resulting mixture was degassed for 5 min.
  2. extractionafter which it was extracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated in a rotary evaporator
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d6632808a358428e8913facb0596087f
Source dataset
uspto-grants-2011_05
Patent number
US07943640B2

Reaction notes

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