Pyridine → 2-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]phenyl}ethyl methanesulfonate

HRID 734896노트

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HRID 734896 반응식
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]#[C:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][OH:29])=[CH:23][CH:22]=3)=[N:17][CH:18]=2)=[CH:9][CH:8]=1.N1C=CC=CC=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:29][CH2:28][CH2:27][C:24]1[CH:23]=[CH:22][C:21]([C:20]#[C:19][C:16]2[CH:15]=[CH:14][C:13]([C:10]3[CH:11]=[CH:12][C:7]([Cl:6])=[CH:8][CH:9]=3)=[CH:18][N:17]=2)=[CH:26][CH:25]=1)(=[O:4])=[O:3]

참가 물질

6

반응물 4

HCID 1049Pyridine2회HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2회HCID 690578442-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]phenyl}ethanol

생성물 1

HCID 866011402-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]phenyl}ethyl methanesulfonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

0.06 mL (0.75 mmol) of methanesulfonic acid chloride was added dropwise at 0° C. to a solution of 167 mg (0.50 mmol) of 2-{4-[5-(4-chlorophenyl)pyridin-2-ylethynyl]phenyl}ethanol and 0.08 mL (1.00 mmol) of pyridine in 5 mL of DCM and the mixture was then stirred for I hour at 0° C. It was combined again with pyridine (0.08 mL) and methanesulfonic acid chloride (0.06 mL) and stirred for 1 hour at RT. Then it was combined with 0.14 mL (1.00 mmol) of triethylamine and after 20 minutes at RT diluted with ice water. The organic phase was separated off, dried over magnesium sulfate, filtered, and the solvent was eliminated in vacuo. Yield: 185 mg (90% of theoretical); C22H18ClNO3S (M=411.902); calc.: molpeak (M+H)+:412/414 (Cl); found: molpeak (M+H)+:412/414 (Cl); HPLC-MS: 6.27 minutes (method H).

후처리

  1. stirringstirred for 1 hour at RT
  2. customThe organic phase was separated off
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. custom6.27 minutes (method H)

출처 및 근거

ORD 기록
ord-562e00ed531d451f93b4ee974bbba072
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592358B2

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