2-Methyltetrahydrofuran → US9000184, 7, isomer 1

HRID 1468240ノート

反応式

HRID 1468240 の反応式
Br[C:2]1[CH:24]=[C:23]2[C:5]([CH2:6][CH2:7][C:8]3([C:16]42[N:20]=[C:19]([NH2:21])[C:18]([CH3:22])=[N:17]4)[CH2:13][CH2:12][CH:11]([O:14][CH3:15])[CH2:10][CH2:9]3)=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:27]=[N:28][CH:29]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:31]=1.CC([PH+](C(C)(C)C)CCCS([O-])(=O)=O)(C)C.CC1CCCO1.C(=O)([O-])[O-].[K+].[K+]>[Na+].[Na+].Cl[Pd+2](Cl)(Cl)Cl.[Pd].O>[Cl:25][C:26]1[CH:31]=[C:30]([C:2]2[CH:24]=[C:23]3[C:5]([CH2:6][CH2:7][C:8]4([C:16]53[N:20]=[C:19]([NH2:21])[C:18]([CH3:22])=[N:17]5)[CH2:9][CH2:10][CH:11]([O:14][CH3:15])[CH2:12][CH2:13]4)=[CH:4][CH:3]=2)[CH:29]=[N:28][CH:27]=1

参加物

9

反応物 5

HCID 73012-MethyltetrahydrofuranHCID 11430Potassium CarbonateHCID 231578663-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 249491873-(Di-tert-butylphosphonium)propane sulfonateHCID 72714746US9000184, 5, isomer 1

生成物 1

HCID 72714841US9000184, 7, isomer 1

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 178479786HCID 178479786、化合物触媒HCID 962Water溶媒2 回

反応条件

温度
130 °C

実験手順

7′-Bromo-4-methoxy-5″-methyl-3′,4′-dihydrodispiro[cyclohexane-1,2′-naphthalene-1′,2″-imidazol]-4″-amine (Example 5, 0.2 g, 0.51 mmol), 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (123 mg, 0.51 mmol), 3-(di-tert-butylphosphonium)propane sulfonate (0.014 g, 0.05 mmol), sodium tetrachloropalladate(II) (7.54 mg, 0.03 mmol), 2-methyltetrahydrofuran (3 mL) and aq. potassium carbonate (2.0 M, 0.769 mL, 1.54 mmol) were added to microwave vial. The vial was sealed and heated in the MW for 30 min at 130° C. The same amount of ligand and Pd-catalyst were added again and the reaction was heated in the MW for 15 min at 130° C. This procedure was repeated twice more. Water and 2-Me THF were added. The water phase was eliminated and the organic phase was washed once with brine and water. The organic phase was concentrated in vacuo. The product was purified using prep HPLC to give:

後処理

  1. customThe vial was sealed
  2. temperaturethe reaction was heated in the MW for 15 min at 130° C
  3. washthe organic phase was washed once with brine and water
  4. concentrationThe organic phase was concentrated in vacuo
  5. customThe product was purified
  6. customto give

出典と根拠

ORDレコード
ord-48a7d74197bc4ce8bf9f7ba343716eec
出典データセット
uspto-grants-2015_04
特許番号
US09000184B2

反応ノート

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