2-(Tri-n-butylstannyl)oxazole → Methyl 3-amino-6-(oxazol-2-yl)-5-(trifluoromethyl)picolinate

HRID 444946Notes

Reaction equation

HRID 444946 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[CH:9][C:8]([C:12]([F:15])([F:14])[F:13])=[C:7](Br)[N:6]=1)=[O:4].C([Sn](CCCC)(CCCC)[C:22]1[O:23][CH:24]=[CH:25][N:26]=1)CCC>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:11][C:10]1[C:5]([C:3]([O:2][CH3:1])=[O:4])=[N:6][C:7]([C:22]2[O:23][CH:24]=[CH:25][N:26]=2)=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:9]=1

Participants

5

Reactant 2

HCID 154861832-(Tri-n-butylstannyl)oxazoleHCID 58964428Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate2×

Product 1

HCID 67383553Methyl 3-amino-6-(oxazol-2-yl)-5-(trifluoromethyl)picolinate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (Intermediate A4) (500 mg, 1.672 mmol), 2-(tributylstannyl)oxazole (0.704 ml, 3.34 mmol) and tetrakis(triphenylphosphine)palladium(0) (193 mg, 0.167 mmol) in dioxane (10 ml) was heated at reflux for 13 hours. After cooling to room temperature over 8 hours, the solvent was evaporated and the resulting residue triturated with hot methanol to remove a yellow solid impurity. The remaining crude material was used without further purification. LC-MS: Rt 0.95 min; MS m/z 288 [M+H]+; Method 2 minLC_v003.

Workup

  1. temperatureat reflux for 13 hours
  2. customthe solvent was evaporated
  3. customthe resulting residue triturated with hot methanol
  4. customto remove a yellow solid impurity
  5. customThe remaining crude material was used without further purification

Sources & evidence

ORD record
ord-117b6c853cd84bf9852a2ab6fa041bcf
Source dataset
uspto-grants-2013_07
Patent number
US08476269B2

Reaction notes

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