Chlorotrimethylsilane → Methyl 3-(2,5-dimethyl-1H-pyrrol-1-yl)-6-hydroxy-5-(trifluoromethyl)picolinate

HRID 444931Notes

Reaction equation

HRID 444931 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[C:9]([C:20]([O:22][CH3:23])=[O:21])=[N:10][C:11]([O:18]C)=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[Si](Cl)(C)(C)C>C(#N)C>[CH3:7][C:4]1[N:3]([C:8]2[C:9]([C:20]([O:22][CH3:23])=[O:21])=[N:10][C:11]([OH:18])=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 67387130HCID 67387130, compound

Product 1

HCID 178499131Methyl 3-(2,5-dimethyl-1H-pyrrol-1-yl)-6-hydroxy-5-(trifluoromethyl)picolinate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 3-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methoxy-5-(trifluoromethyl)picolinate (100 mg, 0.305 mmol) in acetonitrile (3.05 ml) was treated with KI (202 mg, 1.218 mmol) and TMS-Chloride (0.156 ml, 1.221 mmol) and heated at reflux for 6 hours. The solvent removed was in vacuo and the crude product was dissolved in EtOAc (20 ml) and washed with water (2×10 ml) and brine (10 ml), dried over a phase separator and concentrated in vacuo. Purification of the crude product by chromatography on silica eluting with iso-hexane: EtOAc (gradient of 0 to 30% EtOAc) afforded the title compound as an yellow powder. LC-MS Rt=1.11 mins [M+H]+ 315.4 (Method 2 minLC_v003).

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 hours
  3. customThe solvent removed
  4. dissolutionthe crude product was dissolved in EtOAc (20 ml)
  5. washwashed with water (2×10 ml) and brine (10 ml)
  6. customdried over a phase separator
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude product by chromatography on silica eluting with iso-hexane

Sources & evidence

ORD record
ord-905acb551fb44076848c04323834be28
Source dataset
uspto-grants-2013_07
Patent number
US08476269B2

Reaction notes

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