Trifluoroacetic acid → HCID 74220670, compound

HRID 1051224Notes

Reaction equation

HRID 1051224 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[C:13]([C:17]3[C:18]([O:24][CH3:25])=[N:19][CH:20]=[CH:21][C:22]=3[I:23])[NH:14]2)=[CH:10][C:9]=1[O:26][CH3:27])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[I:23][C:22]1[CH:21]=[CH:20][N:19]=[C:18]([O:24][CH3:25])[C:17]=1[C:13]1[NH:14][C:15]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:26][CH3:27])=[C:8]([NH2:7])[CH:16]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90102936HCID 90102936, compound

Product 1

HCID 74220670HCID 74220670, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [2-(4-iodo-2-methoxy-pyridin-3-yl)-5-methoxy-1H-indol-6-yl]-carbamic acid tert-butyl ester (250 mg, 0.51 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 and then concentrated in vacuo and poured into water. The aqueous phase was extracted three times with ethyl acetate. 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 (50/50 hexanes/ethyl acetate) afforded 2-(4-iodo-2-methoxy-pyridin-3-yl)-5-methoxy-1H-indol-6-ylamine (170 mg, 85%) as a white solid. MH+ 395.0.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 3 h
  3. concentrationconcentrated 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-72b5d3e54f524e7faa451910e30c3f5c
Source dataset
uspto-grants-2016_07
Patent number
US09388166B2

Reaction notes

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