Cesium carbonate → 5-(2,6-Dimethoxyphenyl)-1-(4-((4-methylthiazol-2-yl)oxy)benzyl)pyrrolidin-2-one

HRID 594677ノート

反応式

HRID 594677 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[C:14](=[O:24])[CH2:13][CH2:12]1.Br[C:26]1[S:27][CH:28]=[C:29]([CH3:31])[N:30]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC(C)(C(=O)CC(=O)C(C)(C)C)C>CN1C(=O)CCC1.Cl[Cu].C1(C)C=CC=CC=1.CCOC(C)=O.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[N:15]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][C:26]3[S:27][CH:28]=[C:29]([CH3:31])[N:30]=3)=[CH:21][CH:22]=2)[C:14](=[O:24])[CH2:13][CH2:12]1

参加物

10

反応物 4

HCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 5515412-Bromo-4-methyl-1,3-thiazoleHCID 690819375-(2,6-Dimethoxyphenyl)-1-(4-hydroxybenzyl)pyrrolidin-2-one

生成物 1

HCID 690826245-(2,6-Dimethoxyphenyl)-1-(4-((4-methylthiazol-2-yl)oxy)benzyl)pyrrolidin-2-one

試薬・触媒・溶媒 5

HCID 62652Cuprous chloride触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

In a microwave tube, a mixture of 5-(2,6-dimethoxyphenyl)-1-(4-hydroxybenzyl)pyrrolidin-2-one (prepared as described in example 282; 60 mg; 0.18 mmol), commercially available 2-bromo-4-methylthiazole (65 mg; 0.36 mmol), Cs2CO3 (66 mg; 0.20 mmol), CuCl (9 mg; 0.09 mmol), and commercially available 2,2,6,6-tetramethylheptane-3,5-dione (34 mg; 0.18 mmol) in anh. NMP (1 ml) was sealed and irradiated by microwave (175° C.; 10 min.). Water (1 ml), AcOEt (2 ml), and toluene (1 ml) were added, and the resulting suspension was filtered over a pad of celite. The separated organic layer was dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Subsequent purification by preparative HPLC afforded the target compound. LC-MS (conditions A): tR=0.83 min.; [M+H]+: 424.98 g/mol.

後処理

  1. customwas sealed
  2. customirradiated by microwave (175° C.; 10 min.)
  3. filtrationthe resulting suspension was filtered over a pad of celite
  4. dry with materialThe separated organic layer was dried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customSubsequent purification by preparative HPLC
  8. customafforded the target compound

出典と根拠

ORDレコード
ord-8ef7e825d1c84cb3be3d23f167fca88e
出典データセット
uspto-grants-2016_01
特許番号
US09242970B2

反応ノート

読み込み中…