Methanesulfonic Acid → HCID 67248903, compound

HRID 1039898Notes

Reaction equation

HRID 1039898 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([I:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl[C:14]1[N:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][N:15]=1.CS(O)(=O)=O>O1CCOCC1.C(OCC)(=O)C>[I:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([NH:1][C:14]2[N:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][N:15]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidineHCID 11000339methyl 3-amino-5-iodobenzoate

Product 1

HCID 67248903HCID 67248903, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a flask containing methyl 3-amino-5-iodobenzoate (500 mg, 1.81 mmol) was added a solution of 2-chloro-4-(trifluoromethyl)pyrimidine (379 mg, 2.08 mmol) in dioxane (5.6 mL). Methanesulfonic acid (199 mg, 2.08 mmol) was added and the reaction was heated at 100° C. overnight. The reaction was cooled, diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated. Flash chromatography was used for purification to yield methyl 3-iodo-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}benzoate (538 mg, 1.27 mmol, 71% yield). MS ESI: [M+H]+ m/z 424.0.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customFlash chromatography was used for purification

Sources & evidence

ORD record
ord-f4b85e409a644cbea607150d732c1996
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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