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

HRID 1827479노트

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HRID 1827479 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 80711,2-Dimethoxyethane용매

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온도
70 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-486fec25177a4cb0b8bc85373611b181
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07053107B2

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