Methylamine → 4-Methylamino-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde
Reaction equation
Cl[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[NH:10][CH:11]=[CH:12][C:3]=12.ClC1C(C=O)=C[N:17]=[C:16]2N([Si](C(C)C)(C(C)C)C(C)C)C=CC=12.CN>COC(O)C>[CH3:16][NH:17][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[NH:10][CH:11]=[CH:12][C:3]=12Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
A mixture of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde and 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (2.0 g, from above step), methylamine (40% solution in water, 16 mL, 100 mmol) in methoxy-ethanol (4 mL) is heated at 110° C. in a sealed tube overnight. The reaction mixture is cooled to room temperature and concentrated. The residue is dissolved in HCl solution (1N, 20 mL) and heated at 50° C. After stirring for 1.5 hours at 50° C., the reaction mixture is neutralized with saturated sodium bicarbonate solution to a pH of 8. The solid is collected by filtration and washed with water, then hexanes, dried to afford the title compound as a light yellow solid: MS m/z 176.1 (M+1).
Workup
- temperatureThe reaction mixture is cooled to room temperature
- concentrationconcentrated
- dissolutionThe residue is dissolved in HCl solution (1N, 20 mL)
- temperatureheated at 50° C
- filtrationThe solid is collected by filtration
- washwashed with water
- dry with materialhexanes, dried
Sources & evidence
- ORD record
- ord-907f745ce57b4765843423eebb548528
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589101B2
Reaction notes
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