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

HRID 730262

반응식

HRID 730262 반응식
[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]

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-60e8e49f2bc5411d8bf85588256d7cab
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582657B2

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