Sodium Carbonate → 2-(6-chloro-5-methyl-2-(triethylsilyl)-1H-indol-3-yl)ethanol

HRID 58630노트

반응식

HRID 58630 반응식
[Cl:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5](I)=[C:6]([CH:8]=1)[NH2:7].[CH2:11]([Si:13]([CH2:21][CH3:22])([CH2:19][CH3:20])[C:14]#[C:15][CH2:16][CH2:17][OH:18])[CH3:12].[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>[Cl:1][C:2]1[CH:8]=[C:6]2[C:5]([C:15]([CH2:16][CH2:17][OH:18])=[C:14]([Si:13]([CH2:19][CH3:20])([CH2:21][CH3:22])[CH2:11][CH3:12])[NH:7]2)=[CH:4][C:3]=1[CH3:10]

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27606944-(Triethylsilyl)-3-butyn-1-olHCID 584754055-Chloro-2-iodo-4-methylaniline

생성물 1

HCID 668320342-(6-chloro-5-methyl-2-(triethylsilyl)-1H-indol-3-yl)ethanol수율 79.2%

시약·촉매·용매 3

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

반응 조건

온도
100 °C

실험 절차

5-chloro-2-iodo-4-methylaniline (1.50 g; 5.61 mmol), 4-(triethylsilyl)but-3-yn-1-ol (2.36 mL; 11.22 mmol), Bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.229 g; 0.280 mmol), lithium chloride (0.237 g; 5.61 mmol) and sodium carbonate (1.19 g; 11.22 mmol) were suspended in DMF (14 mL) and the mixture was stirred at 100° C. for 15 hours. The mixture was concentrated under reduced pressure and diluted in ethyl acetate. The organic layer was successively washed with brine, sodium thiosulphate, dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford 1.44 g (79%) of the title compound as a brown oil.

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted in ethyl acetate
  3. washThe organic layer was successively washed with brine, sodium thiosulphate
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude mixture was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-cf662b2f82ea4046ac3dbaf33facd596
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434722B2

반응 노트

불러오는 중…