Cesium fluoride → HCID 55283822, compound

HRID 604633Notes

Reaction equation

HRID 604633 reaction equation
I[C:2]1[C:10]2[CH2:9][O:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:11].[F-].[Cs+].[CH3:14]B(O)O>O1CCOCC1.CCOC(C)=O.O.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[CH3:14][C:2]1[C:10]2[CH2:9][O:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:11]

Participants

8

Reactant 3

HCID 25953Cesium fluorideHCID 139377Methylboronic AcidHCID 57576299HCID 57576299, compound

Product 1

HCID 55283822HCID 55283822, compound

Reagents, catalysts & solvents 4

HCID 178477754HCID 178477754, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-iodo-1,3-dihydro-2-benzofuran-5-amine (563 g, 2.16 mmol) in 1,4-dioxane (15 mL) under N2 was added CsF (1.15 g, 7.56 mmol), MeB(OH)2 (387 g, 6.47 mmol) and PdCl2(DPPF) (176 mg, 0.216 mmol). The mixture was heated at 80° C. for 4 h. The mixture was cooled to room temperature and then diluted with EtOAc (40 mL) and water (40 mL). The mixture was filtered through Celite. The organic layer was separated and the aqueous layer was extracted with EtOAc (2×15 mL). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to afford 4-methyl-1,3-dihydro-2-benzofuran-5-amine. LCMS calc.=150.1; found=149.9 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 6.92 (d, J=7.8 Hz, 1H); 6.66 (d, J=7.9 Hz, 1H); 5.11 (s, 4H); 3.63 (br s, 2H); 2.08 (s, 3H)

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe mixture was filtered through Celite
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×15 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-1dbb2c5dfec740ac96be8770e511ea6f
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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