Trifluoroacetic acid → HCID 74220604, compound

HRID 1051218Notes

Reaction equation

HRID 1051218 reaction equation
C(O[C:6](=O)[N:7]([C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([C:18]3[C:19]([O:25][CH3:26])=[N:20][CH:21]=[CH:22][C:23]=3[I:24])[NH:15]2)=[CH:11][CH:10]=1)C)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[I:24][C:23]1[CH:22]=[CH:21][N:20]=[C:19]([O:25][CH3:26])[C:18]=1[C:14]1[NH:15][C:16]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([NH:7][CH3:6])[CH:17]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90103171HCID 90103171, compound

Product 1

HCID 74220604HCID 74220604, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [2-(4-iodo-2-methoxy-pyridin-3-yl)-1H-indol-6-yl]-methyl-carbamic acid tert-butyl ester (520 mg, 1.08 mmol) in CH2Cl2 (5 mL) was added 2,2,2-trifluoroacetic acid (1 mL) at 25° C. The solution was heated to reflux for 3 h. The solution was concentrated in vacuo and poured into water. The aqueous phase was extracted three times with ethyl acetate and the combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave a brown solid. Flash chromatography (70/30 hexanes/ethyl acetate) afforded [2-(4-iodo-2-methoxy-pyridin-3-yl)-1H-indol-6-yl]-methyl-amine (380 mg, 92%) as a white product. MH+ 379.9.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 3 h
  3. concentrationThe solution was concentrated in vacuo
  4. additionpoured into water
  5. extractionThe aqueous phase was extracted three times with ethyl acetate
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationFiltration
  9. concentrationfollowed by concentration in vacuo
  10. customgave a brown solid

Sources & evidence

ORD record
ord-7f1ece54c791470c8c77f3d45a37523e
Source dataset
uspto-grants-2016_07
Patent number
US09388166B2

Reaction notes

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