Hydrochloric Acid → HCID 58382001, 화합물

HRID 1627993노트

반응식

HRID 1627993 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([Si:13]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[CH:9]=[C:10]([CH2:11][CH3:12])[C:3]=12.[Li]C(CC)C.CN([CH:31]=[O:32])C.Cl.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[C:7]([CH:31]=[O:32])=[CH:6][N:5]=[C:4]2[N:8]([Si:13]([CH:14]([CH3:15])[CH3:16])([CH:20]([CH3:21])[CH3:22])[CH:17]([CH3:19])[CH3:18])[CH:9]=[C:10]([CH2:11][CH3:12])[C:3]=12

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 58382052HCID 58382052, 화합물HCID 178418400CID 53628100

생성물 1

HCID 58382001HCID 58382001, 화합물수율 91.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-70 °C

실험 절차

4-Chloro-3-ethyl-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (1.5 g, 4.45 mmol) in THF (25 mL) was cooled to about −70° C. then the sec-BuLi (1.4 M in cyclohexane, 6.36 mL, 8.90 mmol) was added over about 10 min. The mixture was stirred for about 1.25 h at about −70° C. then DMF (1.00 mL, 13.4 mmol) was added over about 5 min. The mixture was stirred for about 30 min then HCl (4.0 M in 1,4-dioxane, 1.11 mL, 4.45 mmol) was added. The mixture was allowed to warm to rt then saturated aqueous NaHCO3 (50 mL) and EtOAc (50 mL) were added. The layers were separated then the aqueous layer was extracted with EtOAc (25 mL) then the combined organics were extracted with saturated aqueous NaCl (25 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The material was purified on a 80 g silica gel column with 9:1 heptane/EtOAc as an eluent to give 4-chloro-3-ethyl-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (1.48 g, 91%): LC/MS (Table 2, Method g) Rt=2.44 min; MS m/z 365 (M+H)+.

후처리

  1. stirringThe mixture was stirred for about 30 min
  2. temperatureto warm to rt
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (25 mL)
  5. extractionthe combined organics were extracted with saturated aqueous NaCl (25 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe material was purified on a 80 g silica gel column with 9:1 heptane/EtOAc as an eluent

출처 및 근거

ORD 기록
ord-247498361eec4ab68ab7541c9d9ddcef
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785639B2

반응 노트

불러오는 중…