Tetrahydrofuran → 2-[3-(2-methoxy-ethoxy)-phenyl]-5-nitro-1H-pyrrolo[2,3-b]pyridine
Reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:18]#[C:19][C:20]2[C:21]([NH2:29])=[N:22][CH:23]=[C:24]([N+:26]([O-:28])=[O:27])[CH:25]=2)[CH:15]=[CH:16][CH:17]=1.O1CCCC1>CN(C)C=O>[CH3:7][O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:18]2[NH:29][C:21]3=[N:22][CH:23]=[C:24]([N+:26]([O-:28])=[O:27])[CH:25]=[C:20]3[CH:19]=2)[CH:15]=[CH:16][CH:17]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
Potassium tert-butoxide (1.18 g, 10.5 mmol) was added to a solution of 3-[3-(2-methoxy-ethoxy)-phenylethynyl]-5-nitro-pyridin-2-ylamine (1.57 g, 5 mmol) in a 2:1 mixture of tetrahydrofuran and dimethylformamide (75 mL). The mixture was heated at 70° C. for 16 hours then the tetrahydrofuran was removed in vacuo. The mixture was poured onto a pad of silica and eluted with ethyl acetate then 10% methanol in ethyl acetate. The organics were concentrated in vacuo to 5% of their original volume and water (30 mL) was added. The resultant orange solid was filtered and dried to afford 2-[3-(2-methoxy-ethoxy)-phenyl]-5-nitro-1H-pyrrolo[2,3-b]pyridine (1.3 g, 83%).
Workup
- customthe tetrahydrofuran was removed in vacuo
- additionThe mixture was poured onto a pad of silica
- washeluted with ethyl acetate
- concentrationThe organics were concentrated in vacuo to 5% of their original volume and water (30 mL)
- additionwas added
- filtrationThe resultant orange solid was filtered
- customdried
Sources & evidence
- ORD record
- ord-a353330159294f34b21cd76cd5474eb1
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07786113B2
Reaction notes
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