Ethyl Acetate → HCID 89442483、化合物

HRID 2284053ノート

反応式

HRID 2284053 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:20][CH2:21][OH:22])[CH:16]=[C:17](Br)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:23][C:24]1[CH:29]=[CH:28][C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][C:25]=1[C:39](F)(F)F.C([O-])([O-])=O.[Cs+].[Cs+].CC(=O)OCC>O1CCOCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:20][CH2:21][OH:22])[CH:16]=[C:17]([C:27]3[CH:28]=[CH:29][C:24]([F:23])=[C:25]([CH3:39])[CH:26]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 222401762-[4-Fluoro-3-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 67265139tert-Butyl 4-(4-bromo-1-(2-hydroxyethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

生成物 1

HCID 89442483HCID 89442483、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
50 °C

実験手順

A mixture of 4-[4-Bromo-1-(2-hydroxy-ethyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (2000.00 mg; 5.34 mmol; 1.00 eq.), 2-(4-fluoro-3-trifluoromethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (1233.97 mg; 8.02 mmol; 1.50 eq.), mg; 0.53 mmol; 0.10 eq.) and Cs2CO3 (3483 mg, 10.69 mmol) in dioxane 15 ml and water 1.5 ml was purged with argon, added Pd(0)(tBu3)2 (273 mg, 0.53 mmol), stirred at 50° C. for overnight. LC-MS showed desired as major product. Diluted reaction solution with EA 70 ml, washed with brine 30mIX2, separated out organic layer, dried, removed off solvent, got crude product, which was subjected to biotage NASP column (100 g), elated with 40-100% EA in hexane and contained 0.5% TEA in EA, collected title compound 1650 mg, 76%

後処理

  1. additionDiluted
  2. washwashed with brine 30mIX2
  3. customseparated out organic layer
  4. customdried
  5. customremoved off solvent
  6. customcollected title compound 1650 mg, 76%

出典と根拠

ORDレコード
ord-72ccef9dcbce4ecdb21cbe734bbcc118
出典データセット
uspto-grants-2015_09
特許番号
US09145392B2

反応ノート

読み込み中…