Toluene → HCID 86673036, 화합물

HRID 1853276노트

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HRID 1853276 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

HCID 86673036HCID 86673036, 화합물수율 20%

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

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온도
120 °C

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-a614c461a5c6435a99c6c660cddfda8a
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962627B2

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