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Triethylamine → 2-{5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethyl methanesulphonate

HRID 1916711
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인쇄 미리보기

반응식

HRID 1916711 반응식
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([C:21]#[C:22][C:23]3[CH:24]=[C:25]4[C:29](=[CH:30][CH:31]=3)[N:28]([CH2:32][CH2:33][OH:34])[CH:27]=[CH:26]4)=[N:19][CH:20]=2)=[CH:11][CH:10]=1.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C1COCC1.N1C=CC=CC=1>[CH3:35][S:36]([O:34][CH2:33][CH2:32][N:28]1[C:29]2[C:25](=[CH:24][C:23]([C:22]#[C:21][C:18]3[CH:17]=[CH:16][C:15]([C:12]4[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][CH:13]=4)=[CH:20][N:19]=3)=[CH:31][CH:30]=2)[CH:26]=[CH:27]1)(=[O:38])=[O:37]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 673637692-{5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethanol

생성물 1

HCID 865946842-{5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethyl methanesulphonate

시약·촉매·용매 2

HCID 1049Pyridine용매
HCID 8028
Tetrahydrofuran
용매
2회

반응 조건

온도
0 °C

실험 절차

Under an argon atmosphere 7.1 mL (51.5 mmol) triethylamine are added to a solution of 16.0 g (42.9 mmol) 2-{5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethanol in 480 mL THF and 30 mL pyridine and this is cooled to 0° C. Then a solution of 4 mL (51.5 mmol) methanesulphonic acid chloride in 20 mL THF is slowly added dropwise, the mixture is allowed to warm up to RT and stirred for a further 2 h at RT. The reaction solution is filtered and evaporated down i.vac. The residue is combined with 1 L DCM, washed with 400 mL water and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is suspended with 600 mL PE/DCM (5:1), suction filtered and finally dried in the air until a constant weight is obtained.

후처리

  1. temperatureto warm up to RT
  2. filtrationThe reaction solution is filtered
  3. customevaporated down i.vac
  4. washwashed with 400 mL water
  5. dry with materialthe organic phase is dried over Na2SO4
  6. filtrationfiltered
  7. customfinally dried in the air until a constant weight
  8. customis obtained

출처 및 근거

ORD 기록
ord-93d5cc7dd2aa419abcc735b0d1982659
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08618132B2

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