1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-(Azidomethyl)-2-(trifluoromethyl)pyridine

HRID 2070999노트

반응식

HRID 2070999 반응식
[F:1][C:2]([F:12])([F:11])[C:3]1[N:8]=[CH:7][C:6]([CH2:9]O)=[CH:5][CH:4]=1.P([N:29]=[N+:30]=[N-:31])(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[N:29]([CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:12])([F:11])[F:1])=[N:8][CH:7]=1)=[N+:30]=[N-:31]

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123414Diphenylphosphoryl azideHCID 36138956-(Trifluoromethyl)pyridine-3-methanol

생성물 1

HCID 866017575-(Azidomethyl)-2-(trifluoromethyl)pyridine수율 100.7%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
0 °C

실험 절차

A mixture of (6-(trifluoromethyl)pyridin-3-yl)methanol (2.0 g, 11.3 mmol) and diphenyl phosphorazidate (2.93 mL, 14 mmol) was dissolved in dry toluene (20 mL). The mixture was cooled to 0° C. under Argon, and neat DBU (2.1 mL, 14 mmol) was added. The reaction mixture was stirred for 2 h at 0° C. and then at rt for 16 h. The resulting two-phase mixture was washed with water and extracted with EtOAc. The combined organic layer was concentrated in vacuo and purified by silica gel chromotography afford 5-(azidomethyl)-2-(trifluoromethyl)pyridine (2.3 g, quantitative yield) of a light yellow oil: 1H NMR (300 MHz, CDCl3+CD3OD), d: 8.686 (m, 1H), 7.853 (m, 1H), 7.723 (d, J=8.1 Hz, 1H), 4.518 (s, 2H).

후처리

  1. waitat rt for 16 h
  2. washThe resulting two-phase mixture was washed with water
  3. extractionextracted with EtOAc
  4. concentrationThe combined organic layer was concentrated in vacuo
  5. custompurified by silica gel chromotography

출처 및 근거

ORD 기록
ord-6cc7529b4df1460fa02d474afc7c44aa
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299267B2

반응 노트

불러오는 중…