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

Triphenylphosphine → 5-[4-fluoro-3-(1-methyl-1H-[1,2,3]triazol-4-ylmethoxy)phenyl]-2-trifluoromethyl[1,8]naphthyridine

HRID 1061836
노트
인쇄 미리보기

반응식

HRID 1061836 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[N:13][C:14]([C:18]([F:21])([F:20])[F:19])=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1[OH:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH3:56][N:57]1[CH:61]=[C:60]([CH2:62]O)[N:59]=[N:58]1>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][N:11]=[C:12]3[C:17]=2[CH:16]=[CH:15][C:14]([C:18]([F:19])([F:20])[F:21])=[N:13]3)=[CH:4][C:3]=1[O:22][CH2:62][C:60]1[N:59]=[N:58][N:57]([CH3:56])[CH:61]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 126543491-Methyl-1H-1,2,3-triazole-4-methanolHCID 222853142-Fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenol

생성물 1

HCID 102724985-[4-fluoro-3-(1-methyl-1H-[1,2,3]triazol-4-ylmethoxy)phenyl]-2-trifluoromethyl[1,8]naphthyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2-Fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenol (50.0 mg, 0.16 mmol), resin-bound triphenylphosphine (180 mg of 3 mmol/g resin, 5.4 mmol), diisopropylazodicarboxylate (76.8 μL, 78.8 mg, 0.40 mmol) and 1-methyl-1H-1,2,3-triazole-4-methanol (prepared as described in WO 0023449, 22.0 mg, 0.20 mmol) were stirred together in THF (3 mL) at room temperature overnight. The mixture was filtered, and the filtrate was diluted with dichloromethane (15 mL), was washed with 1 N sodium hydroxide (2×10 mL), was dried over magnesium sulfate and was concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with 2.5% methanol in dichloromethane, affording 5-[4-fluoro-3-(1-methyl-1H-[1,2,3]triazol-4-ylmethoxy)phenyl]-2-trifluoromethyl[1,8]naphthyridine as a colourless solid, which was recrystallised from ethyl acetate/isohexane (26.7 mg, 41%). δH (360 MHz, CDCl3) 4.13 (3H, s), 5.35 (2H, s), 7.03-7.07 (1H, m), 7.25-7.31 (1H, m), 7.38 (1H, dd, J 2.1 and 7.7), 7.54 (1H, d, J 4.6), 7.70 (1H, s), 7.86 (1H, d, J 8.8), 8.53 (1H, d, J 8.8), 9.26 (1H, d, J 4.2). m/z (ES+) 404 [MH]+.

후처리

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was diluted with dichloromethane (15 mL)
  3. washwas washed with 1 N sodium hydroxide (2×10 mL)
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationwas concentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with 2.5% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-94d9752d35dc4c6b8d87f44f70dbb08f
출처 데이터셋
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06960598B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트