홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Triethylamine → 3,6-Dichloro-2-[(6-chloropyridin-3-ylthio)(pyridin-4-yl)methyl]pyridine

HRID 2080431
노트
인쇄 미리보기

반응식

HRID 2080431 반응식
[Cl:1][C:2]1[C:3]([CH:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)O)=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[Cl:29][C:30]1[N:35]=[CH:34][C:33]([SH:36])=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>CCCCCC.C(OCC)(=O)C.CN(C)C=O.ClCCl>[Cl:1][C:2]1[C:3]([CH:9]([S:36][C:33]2[CH:34]=[N:35][C:30]([Cl:29])=[CH:31][CH:32]=2)[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 14158786-Chloropyridine-3-thiolHCID 23028600(3,6-Dichloropyridin-2-yl) (pyridine-4-yl)methanol

생성물 1

HCID 231147773,6-Dichloro-2-[(6-chloropyridin-3-ylthio)(pyridin-4-yl)methyl]pyridine
수율 36%

시약·촉매·용매 4

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

To a dichloromethane (3 ml) solution of the (3,6-dichloropyridin-2-yl)(pyridin-4-yl)methanol (153 mg, 0.60 mmol) obtained in Referential Example 25 were added triethylamine (0.167 ml, 1.20 mmol) and methanesulfonyl chloride (0.070 ml, 0.90 mmol) sequentially at 0° C. The resulting mixture was stirred at room temperature for 2 hours. After the reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate, the organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. To an N,N-dimethylformamide (3 ml) solution of the residue thus obtained were added an N,N-dimethylformamide (2 ml) solution of 6-chloro-3-pyridinethiol and then, potassium carbonate (100 mg, 0.72 mmol). The resulting mixture was stirred at room temperature for 18 hours. To the reaction mixture was added ethyl acetate. The resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography. The fraction obtained from the hexane:ethyl acetate=7:3 eluate was concentrated under reduced pressure to give the title compound (83 mg, 0.22 mmol, 36%) as a yellow oil.

후처리

  1. washAfter the reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customTo an N,N-dimethylformamide (3 ml) solution of the residue thus obtained
  6. stirringThe resulting mixture was stirred at room temperature for 18 hours
  7. washThe resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customThe residue thus obtained
  12. concentrationethyl acetate=7:3 eluate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b7e2d75d18b740dfab71ad19312a5e74
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07932271B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트