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

Toluene → 4-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine

HRID 910889
노트
인쇄 미리보기

반응식

HRID 910889 반응식
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18](Cl)[CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([NH:1][C:2]2[S:3][CH:4]=[C:5]([CH3:7])[N:6]=2)[CH:17]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 534041974-(Benzyloxy)-2-chloropyridine

생성물 1

HCID 866347144-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine수율 48%

시약·촉매·용매 3

HCID 636044
1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
촉매
HCID 9811564Bis(dibenzylideneacetone)palladium촉매
HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

A 250 mL round-bottomed flask was charged with 2-amino-4-methylthiazole (43.8 mL, 17.5 mmol), 4-(benzyloxy)-2-chloropyridine (4.23 g, 19.3 mmol), potassium phosphate (4.09 g, 19.3 mmol), and toluene (44 mL), and the reaction mixture was degassed with nitrogen. Tris(dibenzylideneacetone)-dipalladium (0) (0.401 g, 0.438 mmol) and 9,9-dimethyl-4,5-bis(diphenyl-phosphino)-xanthene (0.279 g, 0.482 mmol) were added, and the reaction mixture was degassed with nitrogen. The reaction mixture was warmed to 90° C., degassed water (15 mL) was added, and reaction mixture was stirred at 90° C. overnight. Water was added, and the reaction mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and filtered through a small plug of silica gel, and the filtrate was concentrated down to 50 mL of ethyl acetate and filtered to afford 4-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (2.50 g, 47.5% yield) as a white solid. 1H NMR (CDCl3) δ 9.29 (bs, 1H), 8.15 (d, 1H), 7.39 (m, 4H), 7.35 (m, 1H), 6.53 (dd, 1H), 6.41 (d, 1H), 6.36 (d, 1H), 5.07 (s, 2H), 2.33 (s, 3H). Mass spectrum (esi) m/z=298 (M

후처리

  1. customthe reaction mixture was degassed with nitrogen
  2. customthe reaction mixture was degassed with nitrogen
  3. customdegassed water (15 mL)
  4. additionwas added
  5. customreaction mixture
  6. extractionthe reaction mixture was extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered through a small plug of silica gel
  9. concentrationthe filtrate was concentrated down to 50 mL of ethyl acetate
  10. filtrationfiltered

출처 및 근거

ORD 기록
ord-9e1bc0a8e00348de9b492dea08001071
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08022222B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트