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

HRID 1585886
Notes
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Reaction equation

HRID 1585886 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 241
Benzene
Solvent

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-39614d8c3428409ea4a574a54f4724ae
Source dataset
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05939439

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes