Tributylstannane → HCID 70276982, compound

HRID 2289642Notes

Reaction equation

HRID 2289642 reaction equation
C1(OC(=S)O[CH:10]([C:35]2[CH:40]=[CH:39][N:38]([C:41]3[CH:46]=[CH:45][CH:44]=[C:43]([Cl:47])[CH:42]=3)[C:37](=[O:48])[CH:36]=2)[C:11]2[N:12]=[CH:13][N:14]([C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:15]=2)C=CC=CC=1.C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C>C1C=CC=CC=1>[Cl:47][C:43]1[CH:42]=[C:41]([N:38]2[CH:39]=[CH:40][C:35]([CH2:10][C:11]3[N:12]=[CH:13][N:14]([C:16]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:15]=3)=[CH:36][C:37]2=[O:48])[CH:46]=[CH:45][CH:44]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 86755567HCID 86755567, compound

Product 1

HCID 70276982HCID 70276982, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of the thiocarbonate from Step 5 (0.95, 1.4 mmol) in benzene (40 ml) at room temperature was added tributyl tin hydride (1.13 ml, 4.19 mmol) and AIBN (46 mg, 0.28 mmol). The mixture was degassed by bubbling argon through for 15 min and the mixture was heated at 85° C. for 18 hrs while distilling off most of solvent. The residue was chromatographed (silica gel, MeOH: CH2Cl2 2:98 to 4:96 gradient elution) to afford the title compound.

Workup

  1. customThe mixture was degassed
  2. customby bubbling argon through for 15 min
  3. distillationwhile distilling off most of solvent
  4. customThe residue was chromatographed
  5. wash(silica gel, MeOH: CH2Cl2 2:98 to 4:96 gradient elution)

Sources & evidence

ORD record
ord-9764edcf4194436bbd426133a1ea6626
Source dataset
uspto-grants-2000_07
Patent number
US06093737

Reaction notes

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