Methyl iodide → HCID 67281550、化合物

HRID 1187497ノート

反応式

HRID 1187497 の反応式
[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

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 67282369HCID 67282369、化合物

生成物 1

HCID 67281550HCID 67281550、化合物収率 70%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-be0320ca8a9e4de0bab57510b68ec44e
出典データセット
uspto-grants-2014_03
特許番号
US08673943B2

反応ノート

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