Trichloroacetonitrile → (+/-)-1-(5-chloro-3-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indol-7-yl)ethyl 2,2,2-trichloroacetimidate

HRID 913970노트

반응식

HRID 913970 반응식
C1CCN2C(=NCCC2)CC1.[Cl:12][C:13]1[CH:14]=[C:15]2[C:19](=[C:20]([CH:22]([OH:24])[CH3:23])[CH:21]=1)[N:18]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:17]=[C:16]2[C:33]#[N:34].[Cl:35][C:36]([Cl:40])([Cl:39])[C:37]#[N:38]>C1COCC1>[Cl:35][C:36]([Cl:40])([Cl:39])[C:37](=[NH:38])[O:24][CH:22]([C:20]1[CH:21]=[C:13]([Cl:12])[CH:14]=[C:15]2[C:19]=1[N:18]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:32])[CH3:31])[CH:17]=[C:16]2[C:33]#[N:34])[CH3:23]

참가 물질

5

반응물 3

HCID 11011TrichloroacetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57546168(+/-)-5-chloro-7-(1-hydroxyethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole-3-carbonitrile

생성물 1

HCID 57546157(+/-)-1-(5-chloro-3-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indol-7-yl)ethyl 2,2,2-trichloroacetimidate수율 73.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

DBU (0.020 mL, 0.130 mmol) was added to a solution of (±)-5-chloro-7-(1-hydroxyethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole-3-carbonitrile (456 mg, 1.299 mmol) and Trichloroacetonitrile (0.391 mL, 3.90 mmol) in THF (10 mL) and the reaction was stirred for one hour. The solvent was evaporated and the reaction was purified by chromatography on SiO2 with 10:89:1 ethyl acetate/hexanes/triethylamine to give (±)-1-(5-chloro-3-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indol-7-yl)ethyl 2,2,2-trichloroacetimidate (472 mg, 0.953 mmol, 73.3% yield) as a clear oil. 1H-NMR (CDCl3, 400 MHz) δ 8.22 (s, 1H), 7.66 (d, J=2.0 Hz, 1H), 7.61 (s, 1H), 7.52 (d, J=2.0 Hz, 1H), 6.60 (q, J=6.3 Hz, 1H), 6.27 (d, J=11.3 Hz, 1H), 5.25 (d, J=11.3 Hz, 1H), 3.48 (m, 2H), 1.72 (d, J=6.3 Hz, 3H), 0.80-1.05 (m, 2H), −0.02 (s, 9H).

후처리

  1. customThe solvent was evaporated
  2. customthe reaction was purified by chromatography on SiO2 with 10:89:1 ethyl acetate/hexanes/triethylamine

출처 및 근거

ORD 기록
ord-73902588d6f84f9086206146ac4e5f60
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026257B2

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