Iodine chloride → HCID 71150603, compound

HRID 407234Notes

Reaction equation

HRID 407234 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Si](C)(C)C)=[CH:11][CH:10]=2)[N:5]=[C:4]([C:19]([O:21][CH3:22])=[O:20])[C:3]=1[O:23][CH3:24].[I:25]Cl>ClCCCl>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([I:25])=[CH:11][CH:10]=2)[N:5]=[C:4]([C:19]([O:21][CH3:22])=[O:20])[C:3]=1[O:23][CH3:24]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 71150724HCID 71150724, compound

Product 1

HCID 71150603HCID 71150603, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Methyl 4-amino-5-fluoro-3-methoxy-6-(4-(trimethylsilyl)phenyl)picolinate (239 mg, 0.686 mmol) was dissolved in 1,2-dichloroethane (3.4 mL) and iodine monochloride (78 μL, 1.557 mmol). The reaction mixture was stirred at room temperature for 48 h. The mixture was quenched with 10% Na2S2O3 (2 mL) and stirred at room temperature for 1 h. The mixture was extracted with CH2Cl2 (3×5 mL), and the combined organic extracts were dried over Na2SO4 and concentrated in vacuo. The product was purified via RP-HPLC (CH3CN/H2O) to yield the title compound as an orange solid (270 mg, 98%): 1H NMR (400 MHz, DMSO-d6) δ 7.86 (d, J=8.5 Hz, 2H), 7.65-7.53 (m, 2H), 6.54 (s, 2H), 3.86 (s, 3H), 3.77 (s, 3H); 19F NMR (376 MHz, DMSO-d6) δ −140.64; ESIMS m/z 403.61 ([M+H]+).

Workup

  1. customThe mixture was quenched with 10% Na2S2O3 (2 mL)
  2. stirringstirred at room temperature for 1 h
  3. extractionThe mixture was extracted with CH2Cl2 (3×5 mL)
  4. dry with materialthe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe product was purified via RP-HPLC (CH3CN/H2O)

Sources & evidence

ORD record
ord-5947349d814b4c1c9b2b04ef32bff318
Source dataset
uspto-grants-2014_06
Patent number
US08754229B2

Reaction notes

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