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Potassium Phosphate, Tribasic → 2-((1H-indol-5-yl)ethynyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine

HRID 340255
ノート
印刷プレビュー

反応式

HRID 340255 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[C:11][C:12]3[CH:13]=[C:14](Cl)[C:15]([C:18]#[N:19])=[N:16][CH:17]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CC1(C)C(C)(C)OB([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[NH:35]C(=O)OC(C)(C)C)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH:52]1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>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].O.C(O)CCC>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[C:11][C:12]3[CH:17]=[N:16][C:15]4[C:14]([CH:13]=3)=[C:31]3[CH:32]=[CH:33][C:34]([CH3:52])=[CH:29][C:30]3=[N:35][C:18]=4[NH2:19])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 2773231tert-Butyl (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 668923115-((1H-indol-5-yl)ethynyl)-3-chloropicolinonitrile

生成物 1

HCID 668930492-((1H-indol-5-yl)ethynyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 2631-Butanol溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

To a round bottom flask with refluxing condenser were added 5-((1H-indol-5-yl)ethynyl)-3-chloropicolinonitrile (from the previous step) (1 eq.), tert-butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (from Example 5/Step 2) (1.25 eq.), K3PO4 (2 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), and 2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.1 eq.). n-Butanol and water (5:2, 0.2 M) were added, and the content were degassed (vacuum followed by nitrogen flush) for three times. The reaction mixture was stirred vigorously under nitrogen at 100° C. overnight in an oil bath. The content were cooled down and were taken up in 200 mL of water followed by extraction with methylene chloride. Combined organic layers were dried (Na2SO4) and concentrated. Flash chromatography (silica gel, 0-50% EtOAc in CH2Cl2) afforded the product 2-((1H-indol-5-yl)ethynyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine as a yellow solid.

後処理

  1. temperatureTo a round bottom flask with refluxing condenser
  2. customthe content were degassed
  3. custom(vacuum followed by nitrogen flush) for three times
  4. temperatureThe content were cooled down
  5. extractionfollowed by extraction with methylene chloride
  6. dry with materialCombined organic layers were dried (Na2SO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-62dd8a73ca4a49649ab2b576f3759f63
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08895577B2

反応ノート

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