Diethyl Ether → {4-[1-(4-Bromo-phenyl)-2,3-dihydro-1H-indol-5-yloxy]-butyl}-diethyl-amine

HRID 1633672노트

반응식

HRID 1633672 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.[BH3-]C#N.[Na+].CCOCC.[OH-].[Na+]>C(O)(C(F)(F)F)=O.O>[NH3:8].[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:23][CH3:24])[CH2:25][CH3:26])=[CH:14][CH:15]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 18679470{4-[1-(4-Bromo-phenyl)-1H-indol-5-yloxy]-butyl}-diethyl-amine

생성물 2

HCID 222AmmoniaHCID 18679539{4-[1-(4-Bromo-phenyl)-2,3-dihydro-1H-indol-5-yloxy]-butyl}-diethyl-amine수율 76.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6422Trifluoroacetic acid용매

실험 절차

104 mg (0.25 mmol) {4-[1-(4-Bromo-phenyl)-1H-indol-5-yloxy]-butyl}-diethyl-amine in 1 ml TFA were treated with 32 mg (0.5 mmol) NaCNBH3 at 0° C. for 5 min and 30 min at RT. Ether and water were added, followed by 2M NaOH. The inorganic phase was extracted with ether, the combined organic phases were washed with water and dried over Na2SO4. Column chromatography on silica gel with CH2Cl2/MeOH 19:1-1%sat.NH3 in MeOH yielded 40 mg (38%) {4-[1-(4-Bromo-phenyl)-2,3-dihydro-1H-indol-5-yloxy]-butyl}-diethyl-amine as light yellow waxy solid, MS: 417 (MH+, 1Br).

후처리

  1. extractionThe inorganic phase was extracted with ether
  2. washthe combined organic phases were washed with water
  3. dry with materialdried over Na2SO4

출처 및 근거

ORD 기록
ord-3f986c99150c4aa2a40db74674222a8b
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06503907B2

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