Stannous Chloride → HCID 74834217, compound

HRID 2427858Notes

Reaction equation

HRID 2427858 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:37])[C:7]=1[CH:8]=[C:9]([O:28][C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:10]1[C:18]2[C:17]3[CH:19]=[C:20]([N+:23]([O-])=O)[CH:21]=[CH:22][C:16]=3[O:15][C:14]=2[C:13]([O:26][CH3:27])=[CH:12][CH:11]=1.[Sn](Cl)Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:37])[C:7]=1[CH:8]=[C:9]([O:28][C:29](=[O:36])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:10]1[C:18]2[C:17]3[CH:19]=[C:20]([NH2:23])[CH:21]=[CH:22][C:16]=3[O:15][C:14]=2[C:13]([O:26][CH3:27])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 74823169HCID 74823169, compound

Product 1

HCID 74834217HCID 74834217, compoundYield 12.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Benzoic acid 2-(3,5-dichloro-pyridin-4-yl)-1-(4-methoxy-8-nitro-dibenzofuran-1-yl)-vinyl ester (675 mg, 1.26 mmoles) is dissolved in tetrahydrofuran (30 mL). Tin dichloride (SnCl2*2H2O, 2.84 g, 12.6 mmoles) is added and the resulting mixture is stirred at room temperature for 24 hours and at 40° C. for 3 hours. The mixture is diluted with water and a saturated NaHCO3 solution and extracted with DCM; the combined organic layers are dried over sodium sulphate and evaporated to dryness. The crude (468 mg) is purified by preparative HPLC to yield 80 mg of pure product.

Workup

  1. extractiona saturated NaHCO3 solution and extracted with DCM
  2. dry with materialthe combined organic layers are dried over sodium sulphate
  3. customevaporated to dryness
  4. customThe crude (468 mg) is purified by preparative HPLC

Sources & evidence

ORD record
ord-38bc7817a0e142eb826211ba6486a769
Source dataset
uspto-grants-2011_06
Patent number
US07968724B2

Reaction notes

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