Potassium Phosphate, Tribasic → 2-[3-Pyridin-2-ylethynyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-6-ylamino]-benzoic acid methyl ester

HRID 1827479ノート

反応式

HRID 1827479 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[C:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([NH2:18])=[CH:15][CH:16]=2)[N:11]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[N:10]=1.BrC[C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31]([O-:33])=[O:32].[C:38]1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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].C(COC)OC>[CH3:38][O:33][C:31](=[O:32])[C:30]1[CH:34]=[CH:35][CH:36]=[CH:37][C:29]=1[NH:18][C:14]1[CH:13]=[C:12]2[C:17]([C:9]([C:8]#[C:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[N:10][N:11]2[CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:26])[CH3:25])=[CH:16][CH:15]=1

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 4739258HCID 4739258、化合物HCID 235778473-Pyridin-2-ylethynyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-6-ylamine

生成物 1

HCID 235778602-[3-Pyridin-2-ylethynyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-6-ylamino]-benzoic acid methyl ester

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
70 °C

実験手順

A mixture of 3-Pyridin-2-ylethynyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-6-ylamine (560 mg, 1.54 mmol), 2-bromomethylbenzoate (647.5 μL, 4.61 mmol), biphenyl-2-yl-dicyclohexyl-phosphane (107.8 mg, 0.308 mmol), Pd2(dba)3 (70.5 mg, 0.0768 mmol), K3PO4 (816 mg, 3.844 mmol), and dimethoxyethane (1.7 ml), were vacuum flushed with nitrogen, then heated in an oil bath at 70 degrees C. for 24 h. The black mixture was diluted with methylene chloride, and filtered, concentrated, and chromatographed (20% to 40% ethylacetate/hexanes). Yield of yellow/orange oil was 260 mg, 35% for three steps.

後処理

  1. customflushed with nitrogen
  2. additionThe black mixture was diluted with methylene chloride
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed (20% to 40% ethylacetate/hexanes)

出典と根拠

ORDレコード
ord-486fec25177a4cb0b8bc85373611b181
出典データセット
uspto-grants-2006_05
特許番号
US07053107B2

反応ノート

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