Tributylstannane → HCID 59268912, compound

HRID 2061590Notes

Reaction equation

HRID 2061590 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=[O:14])[CH:11]=[CH:10][N:9]1[S:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=1)(=[O:17])=[O:16].CC(N=NC(C#N)(C)C)(C#N)C.C([SnH](CCCC)CCCC)CCC>C1C=CC=CC=1>[F:25][C:24]([F:27])([F:26])[C:21]1[CH:22]=[CH:23][C:18]([S:15]([N:9]2[CH:8]3[C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[CH:10]2[CH2:11][C:12](=[O:14])[CH2:13]3)(=[O:16])=[O:17])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 59268889HCID 59268889, compound

Product 1

HCID 59268912HCID 59268912, compoundYield 12.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of compound 15 (1.65 g, 3.25 mmol) in benzene (300 mL) at 80° C. was added a solution of AIBN (105 mg, 20% mol) and tri(n-butyl)tin hydride (0.86 mL, 3.25 mmol) in benzene (20 mL) over a 2 hour period. The mixture was heated at reflux for 48 h. After evaporation of the solvent, the residue was purified via flash chromatography on silica gel to give a white solid as the product (16) (150 mg, 12%). 1H NMR (CDCl3) δ 7.66 (d, J=8.4 Hz, 2H), 7.41 (d, J=8.4 Hz, 2H), 7.0-6.9 (m, 4H), 5.25 (dd, J=3.3 Hz, 2H), 3.14 (dd, J=4.5, 16.8 Hz, 2H), 2.58 (d, J=16 Hz, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 48 h
  3. customAfter evaporation of the solvent
  4. customthe residue was purified via flash chromatography on silica gel

Sources & evidence

ORD record
ord-e5650891beb241d786da0aa2423b17e0
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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