(E)-trimethyl(2-(tributylstannyl)vinyl)silane → HCID 86668306, compound

HRID 75100Notes

Reaction equation

HRID 75100 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[C:3]=1I.[CH3:15][Si:16]([CH3:33])([CH3:32])/[CH:17]=[CH:18]/[Sn](CCCC)(CCCC)CCCC>ClC(Cl)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[C:3]=1/[CH:18]=[CH:17]/[Si:16]([CH3:33])([CH3:32])[CH3:15]

Participants

5

Reactant 2

HCID 10949136(E)-trimethyl(2-(tributylstannyl)vinyl)silaneHCID 86668303Methyl 4-amino-6-chloro-5-fluoro-3-iodopicolinate

Product 1

HCID 86668306HCID 86668306, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 4-amino-6-chloro-5-fluoro-3-iodopicolinate (0.5 g, 1.513 mmol), (E)-trimethyl(2-(tributylstannyl)vinyl)silane (0.589 g, 1.513 mmol), and bis(triphenylphosphine)palladium(II) chloride (0.106 g, 0.151 mmol) were combined in dichloroethane (3 mL) and stirred at 70° C. overnight. The reaction mixture was concentrated onto celite then purified by flash chromatography (SiO2, hexanes/EtOAc gradient) to afford the title compound (285 mg, 0.941 mmol, 62.2% yield) as an orange solid: mp 103-105° C.; 1H NMR (400 MHz, CDCl3) δ 6.99 (d, J=19.8 Hz, 1H), 6.21 (d, J=19.9 Hz, 1H), 4.72 (s, 2H), 3.89 (s, 3H), 0.19 (s, 9H); 19F NMR (376 MHz, CDCl3) δ −139.10; ESIMS m/z 301 [(M−H)−].

Workup

  1. concentrationThe reaction mixture was concentrated onto celite
  2. customthen purified by flash chromatography (SiO2, hexanes/EtOAc gradient)

Sources & evidence

ORD record
ord-a63d5f6d9e084d368bc55499fda9e9d5
Source dataset
uspto-grants-2014_09
Patent number
US08835409B2

Reaction notes

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