Triethylamine → HCID 86673036、化合物

HRID 1853267ノート

反応式

HRID 1853267 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].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C:54]([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][N:57]=1)#[CH:55].[Na]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13]([C:55]#[C:54][C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][N:57]=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

9

反応物 5

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 137268EthynylpyridineHCID 5360545SodiumHCID 86673023HCID 86673023、化合物

生成物 1

HCID 86673036HCID 86673036、化合物収率 64.1%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

A solution of 7-bromo-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (150 mg, 0.35 mmol), trans-dichlorobis(triphenylphosphine)palladium (22 mg, 0.035 mmol), copper iodide (13 mg, 0.071 mmol), triphenylphosphine (19 mg, 0.071 mmol) in dimethylformamide (3 ml) was degassed with argon for 10 min and then treated with triethylamine (74 μl, 0.53 mmol) and 2-ethynylpyridine (45 μl, 0.45 mmol). The solution was warmed to 120° C. under microwave irradiation (power max=80 W) for 1 hour and then poured onto a saturated aqueous solution of sodium hydrogenocarbonate, extracted with ethyl acetate, washed with water and brine, dried over sodium sulfate and purified by flash chromatography over silica gel (cyclohexane/ethyl acetate: 20-40%) to yield 2-isoquinolin-3-yl-7-(pyridin-2-yl-ethynyl)-chromen-4-one O-tert-butyl oxime (100 mg, 63%) as a yellow solid.

後処理

  1. extractionextracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. custompurified by flash chromatography over silica gel (cyclohexane/ethyl acetate: 20-40%)

出典と根拠

ORDレコード
ord-d073a75929794b2a952922be81893371
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…