Trifluoroacetic acid → methyl 5-(2-(1H-imidazol-2-yl)ethoxy)-6-iodonicotinate

HRID 1498066Notes

Reaction equation

HRID 1498066 reaction equation
C([SiH](CC)CC)C.[I:8][C:9]1[C:18]([O:19][CH2:20][CH2:21][C:22]2[N:23](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:24]=[CH:25][N:26]=2)=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:10]=1.FC(F)(F)C(O)=O>>[NH:23]1[CH:24]=[CH:25][N:26]=[C:22]1[CH2:21][CH2:20][O:19][C:18]1[C:9]([I:8])=[N:10][CH:11]=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58204676methyl 6-iodo-5-(2-(1-trityl-1H-imidazol-2-yl)ethoxy)nicotinate

Product 1

HCID 58204813methyl 5-(2-(1H-imidazol-2-yl)ethoxy)-6-iodonicotinateYield 62.5%

Procedure

Triethylsilane (0.160 mL, 1.00 mmol) was added to a solution of 1.45 g (2.36 mmol) of methyl 6-iodo-5-(2-(1-trityl-1H-imidazol-2-yl)ethoxy)nicotinate in trifluoroacetic acid (30.0 mL, 389 mmol). The mixture was stirred for 4 hours, concentrated in vacuum and triturated with 50 ml of anhydrous ethyl ether. The solid material was collected, washed with several portions of ether and partitioned between 1 M of aqueous sodium carbonate and ethyl acetate. The organic extracts were washed with water, brine, dried over magnesium sulfate and concentrated in vacuum to give a residue (0.55 g, 62%) of methyl 5-(2-(1H-imidazol-2-yl)ethoxy)-6-iodonicotinate. MS(ESI+): 374.0

Workup

  1. concentrationconcentrated in vacuum
  2. customtriturated with 50 ml of anhydrous ethyl ether
  3. customThe solid material was collected
  4. washwashed with several portions of ether
  5. custompartitioned between 1 M of aqueous sodium carbonate and ethyl acetate
  6. washThe organic extracts were washed with water, brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-e140c551eeae47a0a7eb941e0943b75b
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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