Ethanol → Methyl 5-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}-2-chlorobenzoate

HRID 646691ノート

反応式

HRID 646691 の反応式
[Cl:1][C:2]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[NH2:21][C:22]1[C:23]([C:29]([NH:31][CH3:32])=[O:30])=[N:24][C:25](Br)=[CH:26][N:27]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[NH2:21][C:22]1[N:27]=[CH:26][C:25]([C:9]2[CH:10]=[CH:11][C:2]([Cl:1])=[C:3]([CH:8]=2)[C:4]([O:6][CH3:7])=[O:5])=[N:24][C:23]=1[C:29]([NH:31][CH3:32])=[O:30]

参加物

7

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 151481213-Amino-6-bromo-N-methylpyrazine-2-carboxamideHCID 56972886Benzoic acid, 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, methyl ester

生成物 1

HCID 68651344Methyl 5-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}-2-chlorobenzoate収率 56%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
95 °C

実験手順

To a solution of methyl 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.16 g, 0.55 mmol) in toluene (2 mL)) were added 3-amino-6-bromo-N-methyl-2-pyrazincarboxamide (0.13 g, 0.58 mmol), tetralds(triphenylphosphin)palladium(0) (64 mg, 0.06 mmol), ethanol (2 mL), and 2.0 N sodium carbonate (0.42 g, 4.00 mmol). The solution was degassed with nitrogen gas for 3-5 min and heated at 90-100° C. for 2 h. Reaction cooled to room temperature and diluted with ethyl acetate (200 mL). The organic layer was washed water (50 mL) and saturated aqueous sodium chloride (40 mL), dried over magnesium sulfate, filtered, and concentrated to afford crude product. Trituration with methanol (1 mL), filtration and drying gave methyl 5-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}-2-chlorobenzoate (96 mg, 56% yield) as yellow solid. 1H NMR (400 MHz, CDCl3): 8.62 (br s, 1H), 8.28 (d, 1H), 7.92 (dd, 2H), 7.52 (d, 1H), 4.02 (s, 3H), 3.02 (s, 3H); MS (EI) for C14H13N4O2Cl: 321 (MH+).

後処理

  1. customThe solution was degassed with nitrogen gas for 3-5 min
  2. customReaction
  3. temperaturecooled to room temperature
  4. washThe organic layer was washed water (50 mL) and saturated aqueous sodium chloride (40 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford crude product
  9. filtrationTrituration with methanol (1 mL), filtration
  10. customdrying

出典と根拠

ORDレコード
ord-90e8afa896e94634811693ac113e40c4
出典データセット
uspto-grants-2010_04
特許番号
US07704995B2

反応ノート

読み込み中…