Methyl iodide → HCID 67281550, 화합물

HRID 1187497노트

반응식

HRID 1187497 반응식
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[C:13]([CH:16]([OH:21])[C:17]([F:20])([F:19])[F:18])=[CH:12][NH:11][C:10]=1[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](#N)C.C(=O)([O-])[O-].[K+].[K+].CI>ClCCl>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[C:13]([CH:16]([OH:21])[C:17]([F:20])([F:18])[F:19])=[CH:12][N:11]([CH3:23])[C:10]=1[CH3:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 67282369HCID 67282369, 화합물

생성물 1

HCID 67281550HCID 67281550, 화합물수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 3-benzyloxy-2-methyl-5-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (2.07 g, 6.6 mmol), acetonitrile (60 mL), potassium carbonate (2.62 g. 19 mmole) and methyl iodide (15 mL, 0.24 mol) was heated to reflux for 30 min. On cooling to RT, the reaction mixture was filtered over a pad of CELITE™, and the filtrate was concentrated in vacuo to give a solid. The solid was dissolved in dichloromethane, and the resulting solution was washed with brine, dried over Na2S04, filtered and concentrated to afford 3-benzyloxy-1,2-dimethyl5-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (1.48 g, 70% yield, HPLC Method 1 (Example 24), RT=15.4 min, HPLC purity (peak percent area): 99.9% at λ=280 nm). 1H NMR (DMSO-d6+D2O) δ ppm: 7.75 (s, 1H), 7.37, (m, 5H), 5.35 (q, J=7.1 Hz, 1H), 5.01 (m, 2H), 3.63 (s, 3H), 2.18 (s, 3H); MS-ESI (m/z) 328.1 [M+1]+, 220.2, 91.2 (100%).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 30 min
  3. filtrationthe reaction mixture was filtered over a pad of CELITE™
  4. concentrationthe filtrate was concentrated in vacuo
  5. customto give a solid
  6. washthe resulting solution was washed with brine
  7. customdried over Na2S04
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-be0320ca8a9e4de0bab57510b68ec44e
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673943B2

반응 노트

불러오는 중…