Ethyl Bromide → 1-[4-acetyl-1-(2-ethoxy-4-methoxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone
Reaction equation
[C:1]([C:4]1[C:5]([C:20](=[O:22])[CH3:21])=[C:6]([CH3:19])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[OH:18])[C:8]=1[CH3:9])(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:30][CH3:31]>>[C:1]([C:4]1[C:5]([C:20](=[O:22])[CH3:21])=[C:6]([CH3:19])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH2:30][CH3:31])[C:8]=1[CH3:9])(=[O:3])[CH3:2]Participants
Procedure
Utilizing the general procedure outlined in Example 65, 1-[4-acetyl-1-(2-hydroxy-4-methoxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone (70 mg, 2.3 mmol) reacted with bromoethane (300 μL, excess), in the presence of K2CO3 (50 mg), to afford 1-[4-acetyl-1-(2-ethoxy-4-methoxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone: MS (ESI) 330 (M+H)+. Utilizing the general procedure outlined in Example 48, 1-[4-acetyl-1-(4-ethoxy-2-methoxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone (60 mg) and hydrazine (50 μL) reacted to give 6-(2-ethoxy-4-methoxy-phenyl)-1,4,5,7-tetramethyl-6H-pyrrolo[3,4-d]pyridazine as light yellow solid: 1H NMR (CDCl3, 500 MHz) δ 7.04 (d, 1H), 6.68 (s, 1H), 6.64 (d, 1H), 4.15 (q, 1H), 3.78 (s, 3H), 2.81 (s, 6H), 2.40 (s, 6H), 1.51 (t, 3H); MS (ESI) 326 (M+H)+.
Sources & evidence
- ORD record
- ord-99dbbc1b1a414e1180e5fdaf751d66e2
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07465730B2
Reaction notes
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