1-Iodopropane → HCID 67532979, compound

HRID 2358104Notes

Reaction equation

HRID 2358104 reaction equation
[Cl:1][C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1.I[CH2:19][CH2:20][CH3:21].[BH4-].[Na+]>C(=O)([O-])[O-].[Na+].[Na+]>[Cl:1][C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[CH2:13][CH2:14][N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH:17]=1

Participants

5

Reactant 3

HCID 336431-IodopropaneHCID 4311764Sodium borohydrideHCID 57448059HCID 57448059, compound

Product 1

HCID 67532979HCID 67532979, compound

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Conditions

Temperature
100 °C

Procedure

To neat 4-[2-chloro-3-(methylsulfonyl)phenyl]-pyridine (1.0 g, 3.8 mmol) was added 1-iodopropane (5 ml) and the resulting mixture was heated at 100° C. for 2 h. Excess 1-iodopropane was evaporated under reduced pressure and ethanol (60 ml) was added. The mixture was cooled to −20° C. and sodium borohydride (1.3 g, 38 mmol) was added in portions. The resulting mixture was stirred for 1 h, after which aqueous sodium carbonate (10%, 50 ml) was added. The aqueous phase was extracted with ethylacetate (3×100 ml) and the combined organic phases was dried (MgSO4), filtered and evaporated to dryness. The residue was purified by flash column chromatography (ethylacetate/methanol, 1:1) to give the title compound (0.5 g). MS m/z (rel. intensity, 70 eV) 313 (M+, 18), 286 (39), 285 (17), 284 (bp), 128 (12).

Workup

  1. customExcess 1-iodopropane was evaporated under reduced pressure and ethanol (60 ml)
  2. additionwas added
  3. temperatureThe mixture was cooled to −20° C.
  4. extractionThe aqueous phase was extracted with ethylacetate (3×100 ml)
  5. dry with materialthe combined organic phases was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by flash column chromatography (ethylacetate/methanol, 1:1)

Sources & evidence

ORD record
ord-df0e3815e3ca4342b903d3cb34f39826
Source dataset
uspto-grants-2010_07
Patent number
US07763639B2

Reaction notes

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