Benzyl azide → 1-Benzyl-5-(4-fluorophenyl)-4-(tributylstannyl)-1H-1,2,3-triazole

HRID 240770노트

반응식

HRID 240770 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.[CH2:10]([Sn:14]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:18][CH2:19][CH2:20][CH3:21])N(C)C)[CH2:11][CH2:12][CH3:13].[CH2:26]([N:33]=[N+:34]=[N-:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:26]([N:33]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[C:9]([Sn:14]([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:22][CH2:23][CH2:24][CH3:25])[N:35]=[N:34]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

4

반응물 3

HCID 12152Benzyl azideHCID 5226271-Ethynyl-4-fluorobenzeneHCID 11034994Dimethylaminotri-n-butyltin

생성물 1

HCID 689915921-Benzyl-5-(4-fluorophenyl)-4-(tributylstannyl)-1H-1,2,3-triazole

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온도
50 °C

실험 절차

4-Fluorophenyl acetylene (525 mg, 4.37 mmol) was added to 1,1,1-tributyl-N,N-dimethylstannanamine (1.46 g, 4.37 mmol), and the mixture was stirred in a sealed vial at 50° C. for 2 hours. The mixture was cooled to ambient temperature, and the vial was stirred unsealed for 10 minutes. Benzyl azide (850 μL, 6.80 mmol) was added, and the vial was resealed and heated to 130° C. overnight. The mixture was purified by silica gel chromatography eluting with a gradient of 5-35% ethyl acetate in hexanes to afford the title compound. MS (ESI+) m/z 544.4 (M+H)+.

후처리

  1. temperatureThe mixture was cooled to ambient temperature
  2. stirringthe vial was stirred unsealed for 10 minutes
  3. temperatureheated to 130° C. overnight
  4. customThe mixture was purified by silica gel chromatography
  5. washeluting with a gradient of 5-35% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-d3fb472d1f604ee7b3a78794e7b2710c
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648069B2

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