Water → N-Benzyl-N',N'-dimethyl-N-[3-(1-trityl-1H-benzotriazol-5-yl)-benzyl]-propane-1,3-diamine

HRID 1864773Notes

Reaction equation

HRID 1864773 reaction equation
Br[C:2]1[CH:29]=[CH:28][C:5]2[N:6]([C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:7]=[N:8][C:4]=2[CH:3]=1.[CH2:30]([N:37]([CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[C:47](B)[CH:46]=1)[CH2:38][CH2:39][CH2:40][N:41]([CH3:43])[CH3:42])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O.C(Cl)Cl>O1CCOCC1.C(OCC)C>[CH2:30]([N:37]([CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([C:2]2[CH:29]=[CH:28][C:5]3[N:6]([C:9]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:7]=[N:8][C:4]=3[CH:3]=2)[CH:46]=1)[CH2:38][CH2:39][CH2:40][N:41]([CH3:43])[CH3:42])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

8

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 687506515-Bromo-1-trityl-1H-benzo[D][1,2,3]triazoleHCID 178419144HCID 178419144, compound

Product 1

HCID 68748346N-Benzyl-N',N'-dimethyl-N-[3-(1-trityl-1H-benzotriazol-5-yl)-benzyl]-propane-1,3-diamineYield 21.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromo-1-trityl-1H-benzotriazole (220 mg, 0.5 mmol), N-benzyl-N-(3-boranyl-benzyl)-N′,N′-dimethyl-propane-1,3-diamine (180 g, 0.55 mmol), and cesium carbonate solution in water (2M, 1 mL, 2 mmol) taken altogether in 10 mL of dioxane was degassed (evacuate in vacuo and pressurize with argon, two times) and PdCl2(dppf).DCM (21 mg, 0.025 mmol) was added and the mixture was degassed two more times as described above. The resulting mixture was heated at 90° C. for 3 h, then it was allowed to cool to room temperature and the volatiles were removed in vacuo. The residue was partitioned between dichloromethane and water. The aqueous phase was extracted with dichloromethane and the combined organic phases were dried over MgSO4, filtered and evaporated to give the crude product. Chromatography on silica gel (elution with methanol/dichloromethane) followed by trituration of the material obtained with diethyl ether gave 68 mg of the title compound.

Workup

  1. customwas degassed
  2. custom(evacuate in vacuo and pressurize with argon, two times) and PdCl2(dppf)
  3. customthe mixture was degassed two more times
  4. temperatureto cool to room temperature
  5. customthe volatiles were removed in vacuo
  6. customThe residue was partitioned between dichloromethane and water
  7. extractionThe aqueous phase was extracted with dichloromethane
  8. dry with materialthe combined organic phases were dried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customto give the crude product

Sources & evidence

ORD record
ord-d3e2261725374369839fb1fec319aee9
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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