1-Butanol → HCID 59640848, compound

HRID 549215Notes

Reaction equation

HRID 549215 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+].[O:25]1[C:29]2[CH:30]=[CH:31][C:32](B(O)O)=[CH:33][C:28]=2[O:27][CH2:26]1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[O:25]1[C:29]2[CH:30]=[CH:31][C:32]([C:4]3[C:3]([F:13])=[C:2]([Cl:1])[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]=3)=[CH:33][C:28]=2[O:27][CH2:26]1

Participants

8

Reactant 4

HCID 2631-ButanolHCID 10796Cesium carbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 59640842HCID 59640842, compound

Product 1

HCID 59640848HCID 59640848, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-chloro-3-fluoro-2-iodo-quinoline (from Example 1, step D, 0.127 g, 0.41 mmol) in toluene (5 mL) was added n-butanol (2 mL), water (3 mL) and cesium carbonate (0.404 g, 1.2 mmol). The resulting mixture was degassed for 5 min., after which tetrakis(triphenylphosphine)palladium(0) (0.002 g, 5 mol %) and benzo[1,3]dioxole-5-boronic acid (0.086 g, 0.4 mmol) were added. The reaction mixture was stirred at 50° C. for 24 h. and then 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 (0.070 g, 57%). MS (ES) 302 (M+H)+.

Workup

  1. customThe resulting mixture was degassed for 5 min.
  2. extractionextracted 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-ae5ec0de9ce9422dbedc106cc1d7014f
Source dataset
uspto-grants-2011_05
Patent number
US07943640B2

Reaction notes

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