Aniline → HCID 89812927、化合物

HRID 1481141ノート

反応式

HRID 1481141 の反応式
[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]

参加物

9

反応物 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

生成物 1

HCID 89812927HCID 89812927、化合物

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
135 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c3afb1eb8d914a5693ac870522a2f2c6
出典データセット
uspto-grants-2016_08
特許番号
US09409892B2

反応ノート

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