1,4-Dioxane → HCID 86667837、化合物

HRID 1913231ノート

反応式

HRID 1913231 の反応式
[CH3:1][Si:2]([CH3:39])([CH3:38])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:8]1[N:13]2[N:14]=[CH:15][C:16](I)=[C:12]2[N:11]=[C:10]([CH:18]2[CH2:23][CH2:22][CH:21]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:20][CH2:19]2)[CH:9]=1.[Cl:40][C:41]1[N:46]=[CH:45][C:44](B2OC(C)(C)C(C)(C)O2)=[CH:43][CH:42]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:1][Si:2]([CH3:39])([CH3:38])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:44]3[CH:45]=[N:46][C:41]([Cl:40])=[CH:42][CH:43]=3)=[C:12]2[N:11]=[C:10]([CH:18]2[CH2:23][CH2:22][CH:21]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:20][CH2:19]2)[CH:9]=1

参加物

7

反応物 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 27947192-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 66733407Ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate

生成物 1

HCID 86667837HCID 86667837、化合物

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

To a 10-20 mL microwave flask was added ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate (Int-5l, 1.41 g, 2.05 mmol), 6-chloropyridine-3-boronic acid pinacol ester (514 mg, 2.15 mmol), K3PO4 (1.31 g, 6.15 mmol), PdCl2(dppf).CH2O2 (167 mg, 0.21 mmol) and 9:1 1,4-dioxane:H2O (10 mL). The flask was flushed with argon and sealed. The reaction was stirred overnight at 100° C. After 18 hours, the reaction was diluted with DCM and washed with H2O. The aqueous was extracted with DCM (x2) and the combined organic layers were dried over Na2SO4. The solvent was reduced in vacuo and the title compound was purified via silica gel chromatography.

後処理

  1. customThe flask was flushed with argon
  2. customsealed
  3. waitAfter 18 hours
  4. additionthe reaction was diluted with DCM
  5. washwashed with H2O
  6. extractionThe aqueous was extracted with DCM (x2)
  7. dry with materialthe combined organic layers were dried over Na2SO4
  8. customthe title compound was purified via silica gel chromatography

出典と根拠

ORDレコード
ord-3b158308c897475fbfc97fc64634885f
出典データセット
uspto-grants-2013_12
特許番号
US08609675B2

反応ノート

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