反応式
C1(C2[C:13]3=[CH:14][NH:15][C:16]4[CH:17]=[CH:18][CH:19]=[C:11]([C:12]=43)[C:10](=[O:20])[NH:9][N:8]=2)C=CC=CC=1.N1C2C=CC=C(C(OC)=O)C=2C=C1.[F:34][C:35]([F:43])([C:39]([F:42])([F:41])[F:40])[C:36](Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].O.NN>ClC(Cl)C.CO.Cl>[F:34][C:35]([F:43])([C:36]1[C:13]2=[CH:14][NH:15][C:16]3[CH:17]=[CH:18][CH:19]=[C:11]([C:12]=32)[C:10](=[O:20])[NH:9][N:8]=1)[C:39]([F:42])([F:41])[F:40]参加物
反応物 5
生成物 1
試薬・触媒・溶媒 3
実験手順
In a manner similar to that described for Compound 28, a solution of methyl indole-4-carboxylate (351 mg, 2.01 mmol) in dichloroethane (7 mL) was treated with pentafluoropropionyl chloride (2.51 mmol) and aluminum chloride (575 mg). The intermediate ketone (50 mg, 0.16 mmol) in MeOH (2 mL) and conc. HCl (0.02 mL) was treated, as described, with hydrazine hydrate (0.1 mL). The reaction was quenched at 0° C. with 1 M NaOAc and the aqueous layer was adjusted to pH=8 with 1 M NaOH. The product was isolated by extraction with CH2Cl2, and recrystallized (CH2Cl2/MeOH/hexanes) to give 1,5-dihydro-3-pentafluoroethyl-[1,2]diazepino[4,5,6-cd]-indol-6-one, 15 mg (28%) as a yellow solid: 1H NMR (300 MHz, d6-DMSO) δ 7.16 (app br t, 1H), 7.54 (m, 2H), 7.65 (m, 1H), 10.87 (s, 1H), 12.15 (s, 1H). HRMS (FAB, Mna+) Calcd for C11H10N3Ona: 352.0674. Found: 352.0668.
後処理
- customThe reaction was quenched at 0° C. with 1 M NaOAc
- customThe product was isolated by extraction with CH2Cl2
- customrecrystallized (CH2Cl2/MeOH/hexanes)
出典と根拠
- ORDレコード
- ord-f3997a6967ca48e8839f7de9ac6390c3
- 出典データセット
- uspto-grants-2005_12
- 特許番号
- US06977298B2
関連ノート
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