Formaldehyde → (2E)-3-[4-(tert-Butyl)phenyl]-N-(1-methylindolin-6-yl)prop-2-enamide

HRID 2105567

反応式

HRID 2105567 の反応式
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[CH2:4][CH2:3]1.[N+]([C:15]1[CH:23]=[C:22]2[C:18]([CH2:19][CH2:20]N2)=[CH:17][CH:16]=1)([O-])=O.[CH2:24]=[O:25].C([BH3-])#N.[Na+].[Al](Cl)(Cl)Cl.O.O.O.O.O.O>O.[Zn].C1COCC1>[C:5]([C:15]1[CH:23]=[CH:22][C:18](/[CH:19]=[CH:20]/[C:24]([NH:11][C:8]2[CH:9]=[C:10]3[C:5]([CH2:4][CH2:3][N:2]3[CH3:1])=[CH:6][CH:7]=2)=[O:25])=[CH:17][CH:16]=1)([CH3:10])([CH3:6])[CH3:4]

参加物

9

反応物 5

HCID 712FormaldehydeHCID 24564Aluminum chloride, hexahydrateHCID 297576-NitroindolineHCID 5003444Sodium cyanoborohydrideHCID 123690481-methyl-2,3-dihydro-1H-indol-6-amine

生成物 1

HCID 10172096(2E)-3-[4-(tert-Butyl)phenyl]-N-(1-methylindolin-6-yl)prop-2-enamide

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

1-Methylindoline-6-ylamine. To a round-bottomed flask was added 6-nitroindoline (1.64 g, 10.0 mmol, Aldrich), 37% aq. formaldehyde (2.35 g, 30.0 mmol, Aldrich) and THF (40 mL). The reaction mixture was magnetically stirred at 25° C. and treated with sodium cyanoborohydride (1.89 g, 30.0 mmol, Aldrich). The reaction mixture was allowed to stir at 25° C. for 30 min, then washed with satd Na2CO3. The aqueous phase was extracted with ethyl ether, the organic phases combined and concentrated in vacuo to a residue. Analogous to the procedure of Goswami, P.; Chowdhury, P.; Indian J Chem, Sect B, 1997, 36 (2), 185-186, the crude residue was dissolved in tetrahydrofuran (60 mL) and added to Zn dust (0.43 g, 6.6 mmol, Aldrich) and AlCl3.6H2O (9.6 g, 40 mmol, Aldrich) in water (2 mL), magnetically stirred at 25° C. The reaction mixture was stirred at 25° C. for 16 h, then filtered. The filtrate was added to cold water (300 mL) and extracted with CH2Cl2 (3×100 mL). The combined organic extract was concentrated in vacuo to provide the title product as a brown solid. MS (ESI, pos. ion) m/z: 149 (M+1).

後処理

  1. stirringto stir at 25° C. for 30 min
  2. washwashed with satd Na2CO3
  3. extractionThe aqueous phase was extracted with ethyl ether
  4. concentrationconcentrated in vacuo to a residue
  5. dissolutionIndian J Chem, Sect B, 1997, 36 (2), 185-186, the crude residue was dissolved in tetrahydrofuran (60 mL)
  6. stirringmagnetically stirred at 25° C
  7. stirringThe reaction mixture was stirred at 25° C. for 16 h
  8. filtrationfiltered
  9. additionThe filtrate was added to cold water (300 mL)
  10. extractionextracted with CH2Cl2 (3×100 mL)
  11. extractionThe combined organic extract
  12. concentrationwas concentrated in vacuo

出典と根拠

ORDレコード
ord-026013273fea4929b37989f19a041f2e
出典データセット
uspto-grants-2009_08
特許番号
US07579347B2

関連ノート

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