1-Iodopropane → HCID 11712446, compound

HRID 426374Notes

Reaction equation

HRID 426374 reaction equation
[C:1]([C:3]1[C:29]([C:30]#[N:31])=[CH:28][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([C:16]#[C:17][Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])=[CH:12][CH:11]=3)[NH:9][C:5]=2[CH:4]=1)#[N:2].[CH2:32]1[CH2:42]CN2C(=NCCC2)C[CH2:33]1.ICCC>CN1C(=O)CCC1>[C:1]([C:3]1[C:29]([C:30]#[N:31])=[CH:28][C:6]2[N:7]([CH2:33][CH2:32][CH3:42])[C:8]([C:10]3[CH:11]=[CH:12][C:13]([C:16]#[C:17][Si:18]([CH:25]([CH3:27])[CH3:26])([CH:19]([CH3:20])[CH3:21])[CH:22]([CH3:23])[CH3:24])=[CH:14][CH:15]=3)=[N:9][C:5]=2[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 336431-Iodopropane3×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene3×HCID 11618716HCID 11618716, compound

Product 1

HCID 11712446HCID 11712446, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

A 20 mL vial was charged with 5d (763 mg, 1.79 mmol), and NMP (10 mL). The vial was capped with a septum and placed in an oil bath heated to 120° C. DBU (267 μL, 1.79 mmol) was added, and the mixture was stirred for 2 min. Then iodopropane (175 μL, 1.79 mmol) was added and the mixture was stirred for 20 min. A second dose of DBU (267 μL, 1.79 mmol), followed by iodopropane (175 μL, 1.79 mmol), was added, and 20 min later, a third identical round of DBU and iodopropane was again added. After the third round of reagents was added and the mixture was stirred for 20 min, the reaction mixture was removed from heat and added to ethyl acetate. The solution was washed three times with water, then washed with brine, dried over Na2SO4, filtered, and concentrated to dryness. The residue was chromatographed (silica, CHCl3), yielding a colorless solid (506 mg, 61%): mp 242-243° C.; 1H NMR (d6-acetone) δ 0.89 (t, J=7.2 Hz, 3H), 1.17-1.19 (m, 21H), 1.86-1.96 (m, 2H), 4.53 (t, J=7.6 Hz, 2H), 7.75 (d, J=8.0 Hz, 2H), 7.91 (d, J=8.0 Hz, 2H), 8.36 (s, 1H), 8.50 (s, 1H); 13C NMR (d6-acetone) δ 10.5, 11.3, 18.4, 23.2, 47.1, 93.1, 106.6, 108.1, 108.3, 116.8, 116.9, 118.3, 125.8, 126.3, 129.6, 129.9, 132.5, 138.5, 145.4, 158.4; Anal. Calcd for C29H34N4Si: C, 74.63; H, 7.34; N, 12.01. Found: C, 74.75; H, 7.32; N, 12.01.

Workup

  1. customThe vial was capped with a septum
  2. customplaced in an oil bath
  3. stirringthe mixture was stirred for 20 min
  4. additionwas added
  5. additionAfter the third round of reagents was added
  6. stirringthe mixture was stirred for 20 min
  7. customthe reaction mixture was removed
  8. temperaturefrom heat
  9. additionadded to ethyl acetate
  10. washThe solution was washed three times with water
  11. washwashed with brine
  12. dry with materialdried over Na2SO4
  13. filtrationfiltered
  14. concentrationconcentrated to dryness
  15. customThe residue was chromatographed (silica, CHCl3)

Sources & evidence

ORD record
ord-94dcd1a033b74d3d9e811a896fdbe99a
Source dataset
uspto-grants-2012_01
Patent number
US08106393B2

Reaction notes

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