Iodoethane → 1-Ethyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde
Reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[CH:10]=[O:11].C([O-])([O-])=O.[Cs+].[Cs+].I[CH2:19][CH3:20]>CN(C)C=O>[CH2:19]([N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[CH:10]=[O:11])[CH3:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
In a separate reaction: To a suspension of 1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde (600 mg, 4.11 mmol) and Cs2CO3 (2675 mg, 8.21 mmol) in N,N-Dimethylformamide (DMF) (20 mL) stirred under nitrogen at 20° C. was added iodoethane (0.498 mL, 6.16 mmol) dropwise during 0.5 min. The reaction mixture was stirred at r.t. for 1 h, TLC showed complete conversion.
Workup
- customIn a separate reaction
- stirringThe reaction mixture was stirred at r.t. for 1 h
Sources & evidence
- ORD record
- ord-cd52baf1bd9949548ad3a9399eb9de8b
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09127003B2
Reaction notes
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