Cyclohexylamine → N-Cyclohexyl-5-(methylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-amine

HRID 1506211Notes

Reaction equation

HRID 1506211 reaction equation
Cl[C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][N:5]=[C:4]2[N:12]([Si](C(C)C)(C(C)C)C(C)C)[CH:13]=[CH:14][C:3]=12.[CH:25]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(N(CC)C(C)C)(C)C>O>[CH:25]1([NH:31][C:2]2[C:3]3[CH:14]=[CH:13][NH:12][C:4]=3[N:5]=[CH:6][C:7]=2[S:8]([CH3:11])(=[O:9])=[O:10])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 712584634-Chloro-5-(methylsulfonyl)-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 71258218N-Cyclohexyl-5-(methylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-amineYield 15%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chloro-5-(methylsulfonyl)-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (61 mg, 0.16 mmol) in cyclohexylamine (200 μL, 1.74 mmol) was stirred with N,N-diisopropylethylamine (40 μL, 0.23 mmol) at 120° C. for 30 minutes The reaction mixture was allowed to cool to room temperature and, after addition of water, extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1→5/1 (v/v)) to give the title compound as a colorless solid (7.0 mg, yield 15%).

Workup

  1. extractionextracted with chloroform
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1→5/1 (v/v))

Sources & evidence

ORD record
ord-e6cdc9bfba7f4063bc1439830d192745
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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