Water → 1-pentyl-1H-pyrrolo[2,3-b]pyridine-2,3-dione
Reaction equation
[CH2:1]([N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[CH:8]=[CH:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].BrN1C(=[O:21])CCC1=O.[OH2:23]>CS(C)=O>[CH2:1]([N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8](=[O:23])[C:7]1=[O:21])[CH2:2][CH2:3][CH2:4][CH3:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A 2-neck round bottom flask (1 L) was charged with 1-pentyl-1H-pyrrolo[2,3-b]pyridine (17.4 g, 92.6 mmol) in anhydrous dimethylsulfoxide (300 mL) and bubbled with nitrogen. To the reaction solution was added N-bromosuccinimide (34.3 g, 193 mmol) in portion over 15 min at 0° C. The reaction mixture was heated at 60° C. for 6 h followed by at ambient temperature for 16 h. The reaction mixture was diluted with water (200 mL) and stirred for 0.5 h followed by extraction with ethyl acetate (3×200 mL). The combined organic layers was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness to give the title compound as a yellow solid, which was crystallized from ether as an orange solid (14.6 g, 72%): 1H NMR (300 MHz, CDCl3) δ 8.41 (dd, 1H), 7.78 (dd, 1H), 7.03 (dd, 1H), 3.79 (t, 2H), 1.77-1.66 (m, 2H), 1.34-1.29 (m, 4H), 0.85 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 219.1, 182.2, 164.0, 158.2, 155.8, 132.8, 119.4, 112.0, 39.3, 28.9, 27.2, 22.3, 13.9.
Workup
- custombubbled with nitrogen
- extractionfollowed by extraction with ethyl acetate (3×200 mL)
- dry with materialThe combined organic layers was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated in vacuo to dryness
Sources & evidence
- ORD record
- ord-8def2c3be1014d1f8bf1f13b53f789e8
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07799798B2
Reaction notes
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