Tributylstannane → 6-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(4-p-methoxybenzyloxybutyl)-1pyridinyl-}-2H-benzo[b]pyran

HRID 487654Notes

Reaction equation

HRID 487654 reaction equation
[C:1]([C:3]1[CH:45]=[CH:44][C:6]2[O:7][C:8]([CH3:43])([CH3:42])[CH:9]=[C:10]([N:11]3[CH:16]=[CH:15][C:14]([CH:17](OC(OC4C=CC=CC=4)=S)[CH2:18][CH2:19][CH2:20][O:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)=[CH:13][C:12]3=[O:41])[C:5]=2[CH:4]=1)#[N:2].N(C(C)(C)C#N)=NC(C)(C)C#N.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:45]=[CH:44][C:6]2[O:7][C:8]([CH3:42])([CH3:43])[CH:9]=[C:10]([N:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][C:23]4[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=4)=[CH:13][C:12]3=[O:41])[C:5]=2[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 190925096-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(1-phenoxythiocarbonyloxy-4-p-methoxybenzyloxybutyl)-1-pyridinyl}-2H-benzo[b]pyran

Product 1

HCID 190925536-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(4-p-methoxybenzyloxybutyl)-1pyridinyl-}-2H-benzo[b]pyranYield 94.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 46 ml of anhydrous toluene, is dissolved 1.44 g of 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-(1-phenoxythiocarbonyloxy-4-p-methoxybenzyloxybutyl)-1-pyridinyl}-2H-benzo[b]pyran obtained in Example 45. Then, 0.76 g of 2,2'-azobisisobutyronitrile and 1.35 g of tri-n-butyltin hydride are added and reacted at 100° C. for 15 minutes. After the reaction, the reaction mixture is directly purified by silica gel column chromatography using 3/2 mixture of ethyl acetate/n-hexane as a developing solvent. Thus, 1.03 g of 6-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(4-p-methoxybenzyloxybutyl)-1pyridinyl-}-2H-benzo[b]pyran is obtained.

Workup

  1. customreacted at 100° C. for 15 minutes
  2. customAfter the reaction
  3. customthe reaction mixture is directly purified by silica gel column chromatography
  4. addition3/2 mixture of ethyl acetate/n-hexane as a developing solvent

Sources & evidence

ORD record
ord-90a844919f0d41cc8e30f194016bf5e2
Source dataset
uspto-grants-1994_03
Patent number
US05296492

Reaction notes

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