5-chloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one → 5-Chloro-2,3-dihydro-1H-pyrrolo[3,2-B]pyridine
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH2:8][C:9](=O)[NH:10][C:5]2=[CH:4][CH:3]=1>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][NH:10][C:5]2=[CH:4][CH:3]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
5-Chloro-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one (78 mg, 0.46 mmol) was dissolved in THF (1.5 mL). BH3 (1M in THF, 0.92 mL, 0.92 mmol) was added and the mixture was stirred at 60° C. for 3 h. The mixture was cooled to room temperature, diluted with THF and quenched with 1N HCl. The mixture was treated with 2N NaOH until basic and was extracted with ether. The organic extracts were dried, filtered and evaporated to afford 20a.
Workup
- temperatureThe mixture was cooled to room temperature
- customquenched with 1N HCl
- additionThe mixture was treated with 2N NaOH until basic and
- extractionwas extracted with ether
- customThe organic extracts were dried
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-c55c26ce67d4440397614d5737f82358
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481731B2
Reaction notes
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