Sodium Chloride → 1-(tert-butyl)-3-((5-chloro-3-(chloromethyl)pyridin-2-yl)methyl)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one
Reaction equation
[C:1]([N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH:7]([CH2:14][C:15]2[C:20]([CH2:21]O)=[CH:19][C:18]([Cl:23])=[CH:17][N:16]=2)[C:6]1=[O:24])([CH3:4])([CH3:3])[CH3:2].CN(C=O)C.S(Cl)([Cl:32])=O.[Na+].[Cl-]>ClCCl>[C:1]([N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH:7]([CH2:14][C:15]2[C:20]([CH2:21][Cl:32])=[CH:19][C:18]([Cl:23])=[CH:17][N:16]=2)[C:6]1=[O:24])([CH3:4])([CH3:3])[CH3:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 56 (5.8 g, 16.8 mmol) in dichloromethane (30 mL) was added DMF (60 μL) and thionyl chloride (2.2 g) at 5° C. The mixture was stirred for 30 min at this temperature followed by addition of 5% aqueous NaCl (30 mL). The organic layer was separated and washed with 5% aqueous NaCl (30 mL). The solvent was removed and the residue was dissolved in heptane (20 mL). The solution was stirred for 30 min and the product was precipitated. The suspension was cooled to 0° C. and filtered to give 57 (5.8 g, 93%) as a solid:
Workup
- customThe organic layer was separated
- washwashed with 5% aqueous NaCl (30 mL)
- customThe solvent was removed
- dissolutionthe residue was dissolved in heptane (20 mL)
- stirringThe solution was stirred for 30 min
- customthe product was precipitated
- filtrationfiltered
Sources & evidence
- ORD record
- ord-d51b4624f36d4d008e1258338165c4e4
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174989B2
Reaction notes
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