Allyl bromide → HCID 67377459, compound

HRID 1951361Notes

Reaction equation

HRID 1951361 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([CH3:11])[N:10]=[C:4]2[C:3]=1[I:12].[H-].[Na+].[CH2:15](Br)[CH:16]=[CH2:17]>C1COCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:17]([NH:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([CH3:11])[N:10]=[C:4]2[C:3]=1[I:12])[CH:16]=[CH2:15]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 49871062HCID 49871062, compound

Product 1

HCID 67377459HCID 67377459, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 23 (250 mg, 0.92 mmol) in anhydrous THF (20 mL), NaH (60% in mineral oil, 44 mg, 1.098 mmol), allyl bromide (133 mg, 1.10 mmol) and tetrabutylammonium bromide (354 mg, 1.10 mmol) were added under argon atmosphere. The mixture was stirred for 15 h at room temperature. After removal of the solvent, the residue was diluted with H2O (20 mL) and extracted with CH2Cl2 (3×20 mL). The CH2Cl2 extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography using CH2Cl2/EtOAc (4/1, v/v) as eluent to afford compound 30 (156 mg, yield: 54%); as an oil; 1H NMR (400 MHz, CDCl3) δ 2.40 (s, 3H), 3.92 (m, 2H), 4.70 (m, 1H), 5.22 (m, 2H), 5.93 (m, 1H), 6.25 (d, 1H, J=7.3 Hz), 7.21 (s, 1H), 7.75 (d, 1H, J=7.3 Hz); 13C NMR (100 MHz, CDCl3) δ 14.5, 46.6, 64.3, 100.7, 109.1, 116.8, 125.7, 134.5, 142.7, 145.8, 146.3. Anal. Calcd for C11H12IN3: C, 42.19; H, 3.86; N, 13.42. Found: C, 42.39; H, 3.95; N: 1328.

Workup

  1. customAfter removal of the solvent
  2. additionthe residue was diluted with H2O (20 mL)
  3. extractionextracted with CH2Cl2 (3×20 mL)
  4. dry with materialThe CH2Cl2 extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-e69430c0e6d24bed8ed1a167f07113cc
Source dataset
uspto-grants-2013_03
Patent number
US08404707B2

Reaction notes

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