Sodium Chloride → 6-(2-(dimethylamino)ethylamino)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile
Reaction equation
[CH3:1][N:2]([CH3:25])[CH2:3][CH2:4][NH:5][C:6]1[N:11]=[C:10]2[N:12]([Si](C(C)C)(C(C)C)C(C)C)[CH:13]=[CH:14][C:9]2=[CH:8][CH:7]=1.[CH3:26][N:27](C=O)C.ClS(N=C=O)(=O)=O.[Na+].[Cl-]>C(#N)C>[CH3:25][N:2]([CH3:1])[CH2:3][CH2:4][NH:5][C:6]1[N:11]=[C:10]2[NH:12][CH:13]=[C:14]([C:26]#[N:27])[C:9]2=[CH:8][CH:7]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
In a 25 mL round-bottomed flask, N1,N1-dimethyl-N2-(1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-6-yl)ethane-1,2-diamine (405 mg, 1.12 mmol) was combined with DMF (14.9 ml) to give a colorless solution. The reaction mixture was cooled to −20° C. and stirred for 5 min. Chlorosulfonyl isocyanate (477 mg, 293 μl, 3.37 mmol, Eq: 3) in acetonitrile (14.9 ml) was added dropwise and the resultant cooled reaction was stirred at −20° C. and stirred for 3 hrs The reaction mixture was poured into 25 mL sat NaCl and extracted with EtOAc (3×20 ml). After evaporation, crude material was purified by flash chromatography (silica gel, 12 g, 5% to 10% MeOH in DCM) to obtain 6-(2-(dimethylamino)ethylamino)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (211 mg, 82%).
Workup
- customto give a colorless solution
- temperaturethe resultant cooled
- customreaction
- stirringwas stirred at −20° C.
- stirringstirred for 3 hrs The reaction mixture
- additionwas poured into 25 mL
- extractionextracted with EtOAc (3×20 ml)
- customAfter evaporation, crude material
- customwas purified by flash chromatography (silica gel, 12 g, 5% to 10% MeOH in DCM)
Sources & evidence
- ORD record
- ord-951d500767ec44cd8e4f1e13aa785394
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08729078B2
Reaction notes
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