Allyltributylstannane → HCID 67457609, compound

HRID 639643Notes

Reaction equation

HRID 639643 reaction equation
[CH2:1]([NH:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:12]=[C:11](Br)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([Sn](CCCC)(CCCC)CCCC)[CH:28]=[CH2:29]>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:29]([C:11]1[N:10]=[C:9]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:12]=1)[CH:28]=[CH2:27]

Participants

5

Reactant 2

HCID 90628AllyltributylstannaneHCID 58948126HCID 58948126, compound

Product 1

HCID 67457609HCID 67457609, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

N*2*,N*4*-Dibenzyl-6-bromo-3-nitro-pyridine-2,4-diamine (1 g, 2.4 mmol) was stirred in anhydrous tetrahydrofuran (20 ml) and the solution degassed with nitrogen prior to the addition of palladium acetate (109 mg, 0.48 mmol) and allyltributyltin (1.1 ml, 3.6 mmol). The reaction mixture was degassed for 10 minutes before heating the suspension at 80° C. for 16 h. The suspension was cooled to ambient temperature, concentrated in vacuo and purified directly by column chromatography on silica, eluting with pentane:EtOAc, 9:1 to afford the title compound as a yellow solid, (696 mg, 77%)

Workup

  1. customthe solution degassed with nitrogen
  2. customThe reaction mixture was degassed for 10 minutes
  3. temperatureThe suspension was cooled to ambient temperature
  4. concentrationconcentrated in vacuo
  5. custompurified directly by column chromatography on silica
  6. washeluting with pentane

Sources & evidence

ORD record
ord-f958a018eb2e4b1db2258a563a6f1595
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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