Dichloromethane → 6-Methyl-5-(6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamido)nicotinic Acid

HRID 335303ノート

反応式

HRID 335303 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[CH:9][C:10]=2[C:11]([NH:13][C:14]2[C:15]([CH3:24])=[N:16][CH:17]=[C:18]([CH:23]=2)[C:19]([O:21]C)=[O:20])=[O:12])[CH:7]=1.[CH3:25][N:26]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[N:27]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)Cl>COCCOC.O>[CH3:24][C:15]1[C:14]([NH:13][C:11]([C:10]2[CH:9]=[N:8][N:6]3[CH:7]=[C:2]([C:29]4[CH:28]=[N:27][N:26]([CH3:25])[CH:30]=4)[CH:3]=[CH:4][C:5]=23)=[O:12])=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[CH:17][N:16]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 71282967Methyl 5-(6-bromopyrazolo[1,5-a]pyridine-3-carboxamido)-6-methylnicotinate

生成物 1

HCID 712833496-Methyl-5-(6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamido)nicotinic Acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
100 °C

実験手順

Methyl 5-(6-bromopyrazolo[1,5-a]pyridine-3-carboxamido)-6-methylnicotinate (step 1) (7 g, 17.99 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (4.49 g, 21.58 mmol) and cesium carbonate (23.44 g, 71.9 mmol) were stirred in 1,2-dimethoxyethane (60 ml) and water (25.00 ml). The mixture was degassed thoroughly refilling with nitrogen. PdCl2(dppf).CH2Cl2 adduct (0.350 g, 0.429 mmol) was added and the mixture was degassed thoroughly refilling with nitrogen, The mixture was stirred at 100° C. for 7 hrs and then cooled to 50° C. and filtered through glass-fiber paper. The filtrate was acidified to pH 5 by the addition of 2M HCl and filtered. The foam residue was dissolved in DCM/MeOH (1:1) and azeotroped with toluene (×2). The resulting solid was dried in a vacuum oven to afford the title compound;

後処理

  1. customThe mixture was degassed thoroughly
  2. customthe mixture was degassed thoroughly
  3. temperaturecooled to 50° C.
  4. filtrationfiltered through glass-fiber paper
  5. additionThe filtrate was acidified to pH 5 by the addition of 2M HCl
  6. filtrationfiltered
  7. dissolutionThe foam residue was dissolved in DCM/MeOH (1:1)
  8. customazeotroped with toluene (×2)
  9. customThe resulting solid was dried in a vacuum oven

出典と根拠

ORDレコード
ord-6fb19a769cd74750b26af5bf58535f52
出典データセット
uspto-grants-2014_11
特許番号
US08883819B2

反応ノート

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