Trifluoroacetic acid → HCID 66986124, compound

HRID 1254023Notes

Reaction equation

HRID 1254023 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=2)[N:4]=[C:3]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.C1C(=O)N([I:30])C(=O)C1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[I:30][C:6]1[N:2]([CH3:1])[C:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[N:4][C:5]=1[C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 66985987HCID 66985987, compound

Product 1

HCID 66986124HCID 66986124, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 4-(1-methyl-2-pyridin-2-yl-1H-imidazol-4-yl)benzoate (12.5 g, 42.6 mmol) was dissolved in methylene chloride (120 mL), to which was added NIS (10.6 g, 47 mmol) and 0.5 mL of TFA. After stirring for 5 min, the reaction was diluted with 120 mL of methylene chloride and quenched with aq NaHCO3. The organic layer was separated, washed with aq Na2S2O3, water, brine, dried over MgSO4, filtered, and concentrated to give 16.3 g of methyl 4-(5-iodo-1-methyl-2-pyridin-2-yl-1H-imidazol-4-yl)benzoate. 1H NMR (500 MHz, (CDCl3): 8.63 (m, 1H), 8.24 (d, 1H), 8.18 (s, 4H), 7.83 (m, 1H), 7.31 (m, 1H), 4.22 (s, 3H), 3.96 (s, 3H). LCMS: [M+1]=420.

Workup

  1. customquenched with aq NaHCO3
  2. customThe organic layer was separated
  3. washwashed with aq Na2S2O3, water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-44cfc51be68f46558e9d6e95102ad6c9
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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