Sodium Carbonate → 2-(2-(triethylsilyl)-5-(trifluoromethyl)-1H-indol-3-yl)ethanol

HRID 925310노트

반응식

HRID 925310 반응식
I[C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:13]([Si:15]([CH2:23][CH3:24])([CH2:21][CH3:22])[C:16]#[C:17][CH2:18][CH2:19][OH:20])[CH3:14].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd](Cl)Cl>[CH2:23]([Si:15]([CH2:13][CH3:14])([CH2:21][CH3:22])[C:16]1[NH:4][C:3]2[C:2]([C:17]=1[CH2:18][CH2:19][OH:20])=[CH:8][C:7]([C:9]([F:12])([F:11])[F:10])=[CH:6][CH:5]=2)[CH3:24]

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27606944-(Triethylsilyl)-3-butyn-1-olHCID 27833222-Iodo-4-(trifluoromethyl)aniline

생성물 1

HCID 668320092-(2-(triethylsilyl)-5-(trifluoromethyl)-1H-indol-3-yl)ethanol수율 61.3%

시약·촉매·용매 3

HCID 24290Palladium Chloride촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 6228Dimethylformamide용매

실험 절차

2-(2-(triethylsilyl)-5-(trifluoromethyl)-1H-indol-3-yl)ethanol was prepared according to method D Step II with 2-iodo-4-(trifluoromethyl)aniline (1.0 g; 3.48 mmol), 4-(triethylsilyl)but-3-yn-1-ol (0.807 mL; 3.83 mmol), Bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.142 g; 0.174 mmol), lithium chloride (0.147 g; 3.48 mmol) and sodium carbonate (0.738 g; 6.97 mmol) in DMF (10 mL). The crude mixture was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane) to afford 0.733 g (61%) of 2-(2-(triethylsilyl)-5-(trifluoromethyl)-1H-indol-3-yl)ethanol as a yellow oil.

후처리

  1. custom2-(2-(triethylsilyl)-5-(trifluoromethyl)-1H-indol-3-yl)ethanol was prepared
  2. customThe crude mixture was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-9f91656bdf814a65b79f4f5818bc3787
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284271B2

반응 노트

불러오는 중…