Thionyl Chloride → HCID 23436836, 화합물

HRID 1405083노트

반응식

HRID 1405083 반응식
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8](O)([CH3:10])[CH3:9].S(Cl)(Cl)=O>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([CH3:10])=[CH2:9]

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 59636235HCID 59636235, 화합물

생성물 1

HCID 23436836HCID 23436836, 화합물수율 61.5%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a stirred solution of Intermediate 42A (1.25 g) in pyridine (38 mL) at 0° C. was added thionyl chloride (38.5 mL, 526.5 mmol). The reaction mixture was then stirred at room temperature overnight, quenched with saturated aqueous sodium bicarbonate solution and extracted with CH2Cl2 (2×20 mL). The combined organics were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude material was purified by silica gel chromatography (80 g BIOTAGE® column, eluting with hexane:CH2Cl2/4:6) to provide Intermediate 42 (705 mg, 61.5% yield). MS (ES): m/z=198.1 [M+H]+. Intermediate 42 was used in the synthesis of Example 227.

후처리

  1. customquenched with saturated aqueous sodium bicarbonate solution
  2. extractionextracted with CH2Cl2 (2×20 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silica gel chromatography (80 g BIOTAGE® column, eluting with hexane:CH2Cl2/4:6)

출처 및 근거

ORD 기록
ord-f31aab35ce204f34b8c20c546f4f0e08
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916553B2

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