Aniline → HCID 89812927, 화합물

HRID 1481141노트

반응식

HRID 1481141 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10](Br)[CH:9]=2)=[O:4].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+].[NH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1>CN(C=O)C.C(Cl)Cl.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:15][C:14]1[C:13]2[C:8](=[CH:9][C:10]([NH:65][C:66]3[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=3)=[CH:11][CH:12]=2)[CH:7]=[N:6][C:5]=1[C:3]([O:2][CH3:1])=[O:4]

참가 물질

9

반응물 4

HCID 6115AnilineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 89813103Methyl 7-bromo-4-hydroxyisoquinoline-3-carboxylate

생성물 1

HCID 89812927HCID 89812927, 화합물

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
135 °C

실험 절차

A mixture of 7-bromo-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester (141.0 mg, 0.50 mmol), xantphos (28.9 mg, 0.05 mmol, Strem), Pd2(dba)3 (22.9 mg, 0.03 mmol, Sigma-Aldrich), Cs2CO3 (488.7 mg, 1.5 mmol) and aniline (0.1 mL, 1 mmol) in DMF (5 mL) was stirred at 135° C. for 16 hours under a nitrogen atmosphere. After cooling to room temperature, the mixture was diluted with CH2Cl2 (50 mL) and H2O (50 mL). The layers were separated and the aqueous layer was extracted twice with CH2Cl2. The combined organic layers were dried over MgSO4, concentrated, and purified by flash chromatography (0-30% MeOH/CH2Cl2) to give the title compound in 62.4 mg. MS: (−) m/z 293.04 (M−1).

후처리

  1. temperatureAfter cooling to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography (0-30% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-c3afb1eb8d914a5693ac870522a2f2c6
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409892B2

반응 노트

불러오는 중…