1,2-Dibromoethane → HCID 10651810, 화합물

HRID 1387054

반응식

HRID 1387054 반응식
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12](Br)=[CH:11][N:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Li]CCCC.[Mg+2].[Br-].[Br-].BrCCBr.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([C:42]([C:44]2[C:45]3[CH:55]=[CH:54][C:53]([O:56][CH2:57][C:58]4[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=4)=[CH:52][C:46]=3[S:47][C:48]=2N(C)C)=[O:43])[CH:33]=[CH:34][C:35]=1[CH2:36][N:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1.[NH4+].[Cl-]>C1COCC1>[CH3:28][O:29][C:30]1[CH:31]=[C:32]([C:42]([C:44]2[C:45]3[CH:55]=[CH:54][C:53]([O:56][CH2:57][C:58]4[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=4)=[CH:52][C:46]=3[S:47][C:48]=2[C:12]2[CH:11]=[N:10][C:9]([O:8][CH2:7][CH2:6][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:14][CH:13]=2)=[O:43])[CH:33]=[CH:34][C:35]=1[CH2:36][N:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1

참가 물질

8

반응물 6

HCID 78391,2-DibromoethaneHCID 25517Ammonium ChlorideHCID 82241Magnesium BromideHCID 105881665-Bromo-2-(2-(pyrrolidin-1-yl)ethoxy)pyridineHCID 106730126-Benzyloxy-2-dimethylaminobenzo[b]thiophen-3-yl 3-Methoxy-4-[(1-pyrrolidinyl)methyl]phenyl KetoneHCID 178418339Butyllithium

생성물 1

HCID 10651810HCID 10651810, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-78 °C

실험 절차

A −78° C. solution of 5-bromopyrid-2-yl 2-(1-pyrrolidinyl)ethyl ether (3.25 g, 12.0 mmol) in 40 mL of anhydrous THF was treated with n-BuLi (8.1 mL, 13.0 mmol, 1.6 M in hexanes). After 1 h, a slurry of MgBr2 [freshly prepared from Mg (365 mg, 15.0 mmol) and 1.3 mL of 1,2-dibromoethane] in 20 mL of anhydrous THF was added. The reaction mixture was stirred at −78° C. for an additional 10 min, and then the cold bath was removed. After 45 min, the Grignard reagent was added dropwise via a cannula to a solution of 6-benzyloxy-2-(dimethylamino)benzo[b]thiophen-3-yl 3-methoxy-4-[(1-pyrrolidinyl)methyl]phenyl ketone (5 g, 10.0 mmol) in 50 mL of THF at 0° C. The resulting mixture was stirred for 2 h at 0° C. and then was allowed to warm to ambient temperature. After 5 h, the reaction mixture was poured into 200 mL of saturated aqueous NH4Cl. The layers were separated, and the aqueous phase was extracted with CHCl3 (3×50 mL). The combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo. Purification by PrepLC (SiO2; gradient of 85:10:5 hexanes-THF-TEA to 75:20:5 hexanes-THF-TEA) afforded 2.9 g (4.48 mmol; 45%) of the title product as a viscous orange oil.

후처리

  1. additionwas added
  2. customthe cold bath was removed
  3. waitAfter 45 min
  4. stirringThe resulting mixture was stirred for 2 h at 0° C.
  5. temperatureto warm to ambient temperature
  6. waitAfter 5 h
  7. customThe layers were separated
  8. extractionthe aqueous phase was extracted with CHCl3 (3×50 mL)
  9. dry with materialThe combined organic phases were dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customPurification by PrepLC (SiO2; gradient of 85:10:5 hexanes-THF-TEA to 75:20:5 hexanes-THF-TEA)

출처 및 근거

ORD 기록
ord-9200e7b1f69b476486fb3b095543590e
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06265575B1

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