Diethyl Ether → 3-Amino-7-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester
Reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:9]=1[NH:10][CH3:11])[C:7]#[N:8].[H-].[Na+].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(OCC)C>CN(C=O)C>[CH2:19]([O:18][C:16]([C:15]1[N:10]([CH3:11])[C:9]2[C:2]([Cl:1])=[CH:3][N:4]=[CH:5][C:6]=2[C:7]=1[NH2:8])=[O:17])[CH3:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
5-Chloro-4-methylamino-nicotinonitrile (340 mg, 2.02 mmol) was dissolved in DMF (5 mL) and the solution cooled in an ice-bath. This solution was treated portionwise with sodium hydride (120 mg, 60% in oil, 3.03 mmol). The ice-bath was removed and stirring continued for 15 minutes at room temperature before treating the mixture with ethyl bromoacetate (508 mg, 3.03 mmol). The reaction mixture was then partitioned between ethyl acetate and water. The organic layer was isolated, washed with water followed by brine then dried (MgSO4) and evaporated to give a solid. Trituration of the resultant solid with diethyl ether gave the title compound (308 mg, 60%) as a cream solid. 1H NMR (CDCl3) 8.90 (1H, s), 8.26 (1H, s), 8.26 (1H, s, br), 4.43 (2H, q, J=7.0 Hz), 4.28 (3H, s), 1.44 (3H, t, J=7.0 Hz)
Workup
- temperaturethe solution cooled in an ice-bath
- customThe ice-bath was removed
- customThe reaction mixture was then partitioned between ethyl acetate and water
- customThe organic layer was isolated
- washwashed with water
- dry with materialthen dried (MgSO4)
- customevaporated
- customto give a solid
Sources & evidence
- ORD record
- ord-0f93dd6deb3d4ffebe42af149fa2214d
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855216B2
Reaction notes
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