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

HRID 1633672ノート

反応式

HRID 1633672 の反応式
[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

参加物

8

反応物 4

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

生成物 2

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-3f986c99150c4aa2a40db74674222a8b
出典データセット
uspto-grants-2003_01
特許番号
US06503907B2

反応ノート

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