Pyrrole-2-carboxaldehyde → Methyl 2-[(2-formyl-1H-pyrrol-1-yl)methyl]pyridine-3-carboxylate
Reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH:8]=[O:9].[CH3:10][O:11][C:12]([C:14]1[C:15]([CH2:20]Cl)=[N:16][CH:17]=[CH:18][CH:19]=1)=[O:13]>CN(C)C=O>[CH3:10][O:11][C:12]([C:14]1[C:15]([CH2:20][N:3]2[CH:7]=[CH:6][CH:5]=[C:4]2[CH:8]=[O:9])=[N:16][CH:17]=[CH:18][CH:19]=1)=[O:13]Participants
Procedure
To a suspension of sodium hydride (5.8 g, 0.12 mol) in dry N,N-dimethyl formamide (25 mL) was added slowly under nitrogen a solution of pyrrole 2-carboxaldehyde (10.5 g, 0.11 mol) in N,N-dimethylformamide (10 mL). The reaction mixture was stirred at room temperature for 30 minutes, then cooled to 5° C. and 2-chloromethyl-pyridine-3-carboxylic acid methyl ester of Step A added slowly while the temperature was being maintained at or below 20° C. After the addition was complete the reaction was stirred at room temperature for 30 minutes. The mixture was evaporated to dryness, and the residue was dissolved in ethyl acetate (250 mL). This solution was washed with water and dried over anhydrous magnesium sulfate. The solvent was then removed in vacuo leaving a dark crystalline solid (23.4 g), which was purified by chromatography on silica gel eluting with a gradient of ethyl acetate/petroleum ether to provide the title compound as a tan crystalline solid (13.75 g), m.p. 91-93° C.
Workup
- temperaturecooled to 5° C.
- temperaturewas being maintained at or below 20° C
- additionAfter the addition
- stirringwas stirred at room temperature for 30 minutes
- customThe mixture was evaporated to dryness
- dissolutionthe residue was dissolved in ethyl acetate (250 mL)
- washThis solution was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was then removed in vacuo
Sources & evidence
- ORD record
- ord-b557bb844b9349e186e37a9aebf5900c
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06900200B2
Reaction notes
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