Tributylstannane → 5-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one

HRID 1421706Notes

Reaction equation

HRID 1421706 reaction equation
C1(OC(=S)O[CH:10]([C:35]2[CH:36]=[CH:37][C:38]([N:41]3[CH:46]=[C:45]([Cl:47])[CH:44]=[CH:43][C:42]3=[O:48])=[N:39][CH:40]=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:45]1[CH:44]=[CH:43][C:42](=[O:48])[N:41]([C:38]2[CH:37]=[CH:36][C:35]([CH2:10][C:11]3[N:12]=[CH:13][N:14]([C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:15]=3)=[CH:40][N:39]=2)[CH:46]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 53650920Thiocarbonic acid O-[(5-chloro-2-oxo-2H-[1,2']bipyridinyl-5'-yl)-(1-trityl-1H-imidazol-4-yl)-methyl] ester O-phenyl ester

Product 1

HCID 702869365-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the thiocarbonate from Step 4 (0.263 g, 0.386 mmol) in benzene (3 ml) at room temperature was added tributyl tin hydride (0.159 ml, 3.74 mmol) and AIBN (0.012 g, 0.50 mmol) and the mixture was heated at 80° C. for 3 hrs. The solvent was evaporated in vacuo. The residue was chromatographed (silica gel, MeOH: CH2Cl2 2:98 to 4:96 gradient elution) to afford the title compound.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was chromatographed
  3. wash(silica gel, MeOH: CH2Cl2 2:98 to 4:96 gradient elution)

Sources & evidence

ORD record
ord-aefe3634d68b40548515319928db9aac
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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