Toluene → HCID 86673036、化合物

HRID 1853276ノート

反応式

HRID 1853276 の反応式
[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14](Br)[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].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(B2OC(C)(C)C(C)(C)O2)CC1.[Cl-].[NH4+:49].[C:50]1([CH3:56])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13]([C:56]#[C:50][C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][N:49]=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

7

反応物 5

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 27580152-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86673027HCID 86673027、化合物

生成物 1

HCID 86673036HCID 86673036、化合物収率 20%

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

反応条件

温度
120 °C

実験手順

A solution of 6-bromo-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (100 mg, 0.236 mmol), palladium acetate (3 mg, 0.014 mmol), potassium phosphate (175 mg, 0.826 mmol), dicyclohexylbiphenylphosphine (8 mg, 0.024 mmol), Cyclopropylboronic acid pinacol ester (99 mg, 0.59 mmol) in toluene (3 ml) was degassed with argon for 10 min. The reactor was sealed and heated at 120° C. for 18 hours. The mixture was poured onto a saturated aqueous solution of ammonium chloride, extracted with ethyl acetate, washed with water and brine, dried over sodium sulfate and purified by flash chromatography over silica gel (cyclohexane/dichloromethane: 0-80%) to yield 2-isoquinolin-3-yl-7-(pyridin-2-yl-ethynyl)-chromen-4-one O-tert-butyl oxime (18 mg, 20%).

後処理

  1. customThe reactor was sealed
  2. extractionextracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. custompurified by flash chromatography over silica gel (cyclohexane/dichloromethane: 0-80%)

出典と根拠

ORDレコード
ord-a614c461a5c6435a99c6c660cddfda8a
出典データセット
uspto-grants-2015_02
特許番号
US08962627B2

反応ノート

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