Potassium Carbonate → tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]-3,6-dihydro-1(2H)-pyridinecarboxylate

HRID 1832262ノート

反応式

HRID 1832262 の反応式
CC(C)(C)C(O[N:6]1[CH2:11][CH:10]=[C:9](B2OC(C)(C)C(C)(C)O2)[CH2:8][CH2:7]1)=O.[C:23]([O-:26])([O-])=[O:24].[K+].[K+].Br[C:30]1[CH:31]=[C:32]([NH:37][C:38](=[O:42])[CH:39]([CH3:41])[CH3:40])[CH:33]=[CH:34][C:35]=1[CH3:36]>CN(C=O)C>[C:38]([NH:37][C:32]1[CH:31]=[CH:30][C:35]([CH3:36])=[C:34]([C:9]2[CH2:8][CH2:7][N:6]([C:23]([O:26][C:35]([CH3:36])([CH3:34])[CH3:30])=[O:24])[CH2:11][CH:10]=2)[CH:33]=1)(=[O:42])[CH:39]([CH3:41])[CH3:40]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 22048859N-(3-Bromo-4-methylphenyl)-2-methylpropanamideHCID 220492871-[(2,2-Dimethylpropanoyl)oxy]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine

生成物 1

HCID 16756287tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]-3,6-dihydro-1(2H)-pyridinecarboxylate収率 124%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a 50-mL RB flask containing 1-[(2,2-dimethylpropanoyl)oxy]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine (500 mg, 1.62 mmol), K2CO3 (670 mg, 4.86 mmol) and PdCl2dppf (155 mg) was added a solution of N-(3-bromo-4-methylphenyl)-2-methylpropanamide (415 mg, 1.62 mmol) in DMF (10.0 mL) at room temperature under argon. The mixture was heated to 80° C. under argon overnight. After cooled to room temperature, the mixture was filtered through celite and the celite was washed with EtOAc (3×20 mL) The filtrates were washed with H2O (20 mL), brine (20 mL), dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified flash chromatography (20% EtOAc/hexane) to give tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]-3,6-dihydro-1(2H)-pyridinecarboxylate (360 mg, 62.0%).

後処理

  1. temperatureAfter cooled to room temperature
  2. filtrationthe mixture was filtered through celite
  3. washthe celite was washed with EtOAc (3×20 mL) The filtrates
  4. washwere washed with H2O (20 mL), brine (20 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified flash chromatography (20% EtOAc/hexane)

出典と根拠

ORDレコード
ord-5c31882ce1ac483c99954110a4466515
出典データセット
uspto-grants-2006_06
特許番号
US07067534B1

反応ノート

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