Triethylamine → HCID 86673036, 화합물

HRID 1853267노트

반응식

HRID 1853267 반응식
[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]

참가 물질

9

반응물 5

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 137268EthynylpyridineHCID 5360545SodiumHCID 86673023HCID 86673023, 화합물

생성물 1

HCID 86673036HCID 86673036, 화합물수율 64.1%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-d073a75929794b2a952922be81893371
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962627B2

반응 노트

불러오는 중…