Cesium fluoride → HCID 86673032、化合物

HRID 1853264ノート

反応式

HRID 1853264 の反応式
[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[O:10][C:9]([C:18]2[N:19]=[CH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2].[F-].[Cs+].[CH:30](/B(O)O)=[CH:31]\[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>COCCOC.CO.ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13](/[CH:30]=[CH:31]/[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:14][CH:15]=2)[O:10][C:9]([C:18]2[N:19]=[CH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 3

HCID 25953Cesium fluorideHCID 5702628Styrylboronic acidHCID 86673023HCID 86673023、化合物

生成物 1

HCID 86673032HCID 86673032、化合物収率 76.2%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
150 °C

実験手順

In a microwave vial, a solution of 7-bromo-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (200 mg, 0.47 mmol), cesium fluoride (213 mg, 1.41 mmol) and trans-styryl boronic acid (160 mg, 1.07 mmol) in 1,2-dimethoxyethane (3.2 ml) and methanol (1.6 ml) was degassed with argon for 20 min and then tetrakis(triphenylphosphine)palladium (30 mg, 0.026 mmol) was added. The vial was sealed and the mixture was heated under microwave irradiation to 150° C. for 5 min. After cooling, the solution was diluted with dichloromethane and absorbed over silica gel for purification by flash chromatography (gradient cyclohexane/dichloromethane: 0-80%) to yield 2-Isoquinolin-3-yl-7-((E)-styryl)-chromen-4-one O-tert-butyl oxime (160 mg, 76%) as a yellow solid.

後処理

  1. customThe vial was sealed
  2. temperatureAfter cooling
  3. customabsorbed over silica gel for purification by flash chromatography (gradient cyclohexane/dichloromethane: 0-80%)

出典と根拠

ORDレコード
ord-e64d892cefb74a4eac05263a9413e8f6
出典データセット
uspto-grants-2015_02
特許番号
US08962627B2

反応ノート

読み込み中…