Lithium hydroxide, monohydrate → CID 89583150

HRID 402770ノート

反応式

HRID 402770 の反応式
[CH3:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([CH2:12][N:13]2[CH2:33][CH2:32][C:16]3([O:20][C:19](=[O:21])[N:18]([C:22]4[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=4)[CH2:17]3)[CH2:15][CH2:14]2)=[C:4](Br)[CH:3]=1.[F:35][C:36]1[C:41]([F:42])=[C:40]([F:43])[CH:39]=[CH:38][C:37]=1B(O)O.O.[OH-].[Li+]>O1CCOCC1.O.C(#N)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:39]2[CH:38]=[CH:37][C:36]([F:35])=[C:41]([F:42])[C:40]=2[F:43])[C:5]([CH2:12][N:13]2[CH2:33][CH2:32][C:16]3([O:20][C:19](=[O:21])[N:18]([C:22]4[CH:31]=[CH:30][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=4)[CH2:17]3)[CH2:15][CH2:14]2)=[CH:6][C:7]=1[C:8]([F:11])([F:9])[F:10]

参加物

7

反応物 3

HCID 168937Lithium hydroxide, monohydrateHCID 27832802,3,4-Trifluorobenzeneboronic acidHCID 66764641Methyl 4-{8-[(4-methyl-5-trifluoromethyl-2-bromophenyl)methyl]-2-oxo-1-oxa-3,8-diazaspiro[4.5]dec-3-yl}benzoate

生成物 1

HCID 89583150CID 89583150収率 42.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

To a solution of methyl 4-{8-[(4-methyl-5-trifluoromethyl-2-bromophenyl)methyl]-2-oxo-1-oxa-3,8-diazaspiro[4.5]dec-3-yl}benzoate (30 mg, 0.055 mmol) in dioxane (1.5 mL) and water (0.5 mL) in a 5 mL microwave reaction vial were added 2,3,4-trifluorophenylboronic acid (20 mg, 0.111 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium (II) dichloride dichloromethane complex (9 mg, 0.011 mmol) and lithium hydroxide mono-hydrate (5 mg, 0.111 mmol). The reaction was heated in a microwave at 120° C. for 15-30 minutes. The crude reaction was diluted with acetonitrile and water, filtered and purified by reverse phase chromatography using a gradient of acetonitrile and water with 0.1% ammonium hydroxide. Lypholization of the desired fractions afforded the title compound (13.4 mg) as a white solid.

後処理

  1. customThe crude reaction
  2. filtrationfiltered
  3. custompurified by reverse phase chromatography

出典と根拠

ORDレコード
ord-094ebcdb0c62463cad257b2162d9bf53
出典データセット
uspto-grants-2014_06
特許番号
US08742110B2

反応ノート

読み込み中…