Ethyl Acetate → {1-[1-(4-methoxy-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile

HRID 552309Notes

Reaction equation

HRID 552309 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([N:10]2[C:14]3=[N:15][C:16]([CH3:27])=[CH:17][C:18](OS(C(F)(F)F)(=O)=O)=[C:13]3[C:12]([CH3:28])=[CH:11]2)=[C:5]([CH3:29])[CH:4]=1.C(N(CC)C(C)C)(C)C.[NH:39]1[CH2:44][CH2:43][CH:42]([CH2:45][C:46]#[N:47])[CH2:41][CH2:40]1.C(OCC)(=O)C>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:29])[C:6]([N:10]2[C:14]3=[N:15][C:16]([CH3:27])=[CH:17][C:18]([N:39]4[CH2:44][CH2:43][CH:42]([CH2:45][C:46]#[N:47])[CH2:41][CH2:40]4)=[C:13]3[C:12]([CH3:28])=[CH:11]2)=[C:7]([CH3:9])[CH:8]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 100119032-(Piperidin-4-yl)acetonitrileHCID 59843342trifluoromethanesulfonic acid 1-(4-methoxy-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl ester

Product 1

HCID 67103732{1-[1-(4-methoxy-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrileYield 56.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of crude trifluoromethanesulfonic acid 1-(4-methoxy-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl ester (1.1 g), N,N-diisopropylethylamine (0.65 g) and piperidin-4-yl-acetonitrile (1.6 g) was heated at 150° C. in a sealed tube for 7 hours. After cooling to room temperature, ethyl acetate and water were poured into the mixture, and separated. The aqueous phase was extracted with ethyl acetate, and the organic phase was dried over MgSO4 and filtered. The filtrate was concentrated under reduced pressure and the residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=3/1) to obtain {1-[1-(4-methoxy-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile (0.58 g) as a pale yellow crystal.

Workup

  1. temperatureAfter cooling to room temperature
  2. customseparated
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialthe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=3/1)

Sources & evidence

ORD record
ord-9166ac52266942a89c3c49465df2f8de
Source dataset
uspto-grants-2011_05
Patent number
US07951811B2

Reaction notes

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