Ethyl Acetate → HCID 90413538, compound

HRID 1746075Notes

Reaction equation

HRID 1746075 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[C:17]3[O:16][C:15]([F:19])([F:18])[O:14][C:13]=3[C:12]([Si](C)(C)C)=[CH:11][CH:10]=2)[N:5]=[C:4]([C:24]([O:26][CH3:27])=[O:25])[C:3]=1[Cl:28].[I:29]Cl.OS([O-])=O.[Na+].C(OCC)(=O)C>ClCCCl>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[C:17]3[O:16][C:15]([F:19])([F:18])[O:14][C:13]=3[C:12]([I:29])=[CH:11][CH:10]=2)[N:5]=[C:4]([C:24]([O:26][CH3:27])=[O:25])[C:3]=1[Cl:28]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24640Iodine chlorideHCID 23665763Sodium BisulfiteHCID 90413465HCID 90413465, compound

Product 1

HCID 90413538HCID 90413538, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
20 °C

Procedure

Methyl 4-amino-3-chloro-6-(2,2-difluoro-7-(trimethylsilyl)benzo[d][1,3]dioxol-4-yl)-5-fluoropicolinate (400 mg, 0.92 mmol) in 1,2-dichloroethane (5 mL) was treated with iodine monochloride (900 mg, 5.5 mmol) and stirred for 20 h at 20° C. The mixture was combined with 10 wt % NaHSO3 solution (30 mL) and ethyl acetate (30 mL). The aqueous phase was extracted with ethyl acetate (15 mL), and the combined organic phases were washed with saturated NaCl (10 mL), dried (Na2SO4) and evaporated to give the title compound as a white solid (430 mg, 96%): mp 156-159° C.; 1H NMR (400 MHz, CDCl3) δ 7.50 (d, J=8.6 Hz, 1H), 7.23 (d, J=8.6 Hz, 1H), 5.02 (s, 2H), 3.99 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −49.22, −137.49; ESIMS m/z 487 ([M+H]+), 485 ([M−H]−).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate (15 mL)
  2. washthe combined organic phases were washed with saturated NaCl (10 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-f26ac84b490140b887a5f40199990738
Source dataset
uspto-grants-2015_10
Patent number
US09149038B2

Reaction notes

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