Benzylamine → N-benzyl-6-methylpyridazin-3-amine

HRID 885943

反応式

HRID 885943 の反応式
Cl[C:2]1[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.[Cl-].[Cl-].[Fe+2].[Pd+2]>[CH2:9]([NH:16][C:2]1[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 3

HCID 7504BenzylamineHCID 2272543-Chloro-6-methylpyridazineHCID 23676156Sodium t-butoxide

生成物 1

HCID 61313509N-benzyl-6-methylpyridazin-3-amine収率 91.3%

試薬・触媒・溶媒 2

HCID 53384307Dichloro[1,1'-bis(di-tert-butylphosphino)ferrocene]palladium(II)触媒HCID 1140Toluene溶媒

反応条件

温度
140 °C

実験手順

To a stirred solution of 3-chloro-6-methylpyridazine (215 mg, 1.66 mmol) and benzylamine (267 mg, 2.5 mmol) in toluene (20 mL) was added sodium tert-butoxide (480 mg, 5.0 mmol) and [1,1′-bis(di-tert-butylphosphino)ferrocene]palladium(II) dichloride (20 mg). The reaction mixture was stirred at 140° C. under microwave irradiation for 2 h, then cooled to room temperature and concentrated in vacuo. The residue was purified by column chromatography (SiO2, 0-100% EtOAc/heptane) to give the title compound (302 mg, 91%) as an off-white solid. δH (CDCl3) 7.25-7.41 (5H, m), 7.02 (1H, d, J 9.0 Hz), 6.55 (1H, d, J 9.0 Hz), 4.91 (1H, s), 4.60 (2H, d, J 5.8 Hz), 2.53 (3H, s). LCMS (ES+) 200 (M+H)+, RT 2.50 minutes (Method 2).

後処理

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography (SiO2, 0-100% EtOAc/heptane)

出典と根拠

ORDレコード
ord-97edd6a3912e4bb496eba53b2e8f2b55
出典データセット
uspto-grants-2012_08
特許番号
US08242116B2

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