Tetrahydrofuran → 5-chloro-7-formyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole-3-carbonitrile

HRID 913968노트

반응식

HRID 913968 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH:11]=C)[CH:10]=1)[N:7]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:6]=[C:5]2[C:21]#[N:22].C[N+]1([O-])CC[O:27]CC1.C1COCC1.I([O-])(=O)(=O)=O.[Na+]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH:11]=[O:27])[CH:10]=1)[N:7]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:6]=[C:5]2[C:21]#[N:22]

참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 575459895-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-7-vinyl-1H-indole-3-carbonitrile

생성물 1

HCID 575462455-chloro-7-formyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole-3-carbonitrile수율 80%

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 180Acetone용매HCID 962Water용매

실험 절차

Osmium tetroxide (0.1 mL, 0.013 mmol) (4% in water) was added to a solution of 5-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-7-vinyl-1H-indole-3-carbonitrile (385 mg, 1.157 mmol) and NMO (271 mg, 2.313 mmol) in Acetone (20 mL) and Water (5 mL). The reaction was stirred at ambient temperature for 2 hours and then THF (10 mL) and sodium periodate (742 mg, 3.47 mmol) were added. The reaction was stirred for 1 hour, and precipitate formed. The solvent was evaporated and the residue was taken up in water (100 mL) and extracted with ethyl acetate (3×20 mL). The organic layers were dried with MgSO4 and evaporated. The residue was purified by chromatography on SiO2 with 10% to 15% ethyl acetate/hexanes to give 5-chloro-7-formyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole-3-carbonitrile (310 mg, 0.926 mmol, 80% yield) as a white solid. 1H-NMR (CDCl3, 400 MHz) δ 10.22 (s, 1H), 8.0 (d, J=2.0 Hz, 1H), 7.84 (d, J=2.0 Hz, 1H), 7.79 (s, 1H), 5.80 (s, 2H), 3.43 (app T, J=8.2 Hz, 2H), 0.84 (app t, J=8.2 Hz, 2H), −0.07 (s, 9H). LC (HPLC method 4): tR=3.68 min.

후처리

  1. stirringThe reaction was stirred for 1 hour
  2. customprecipitate formed
  3. customThe solvent was evaporated
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. dry with materialThe organic layers were dried with MgSO4
  6. customevaporated
  7. customThe residue was purified by chromatography on SiO2 with 10% to 15% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-8ed3dc984538470ebd0f0f4d1b8f27a9
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026257B2

반응 노트

불러오는 중…