Potassium Carbonate → N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79442ノート

反応式

HRID 79442 の反応式
[CH3:1][N:2]1[CH:6]=[C:5](B2OC(C)(C)C(C)(C)O2)[CH:4]=[N:3]1.Br[C:17]1[CH:22]=[CH:21][N:20]2[C:23]([C:26]([NH:28][C:29]3[CH:37]=[CH:36][CH:35]=[C:34]4[C:30]=3[C:31]([CH2:46][CH3:47])=[N:32][N:33]4[CH2:38][C:39]3[CH:43]=[CH:42][N:41]([CH2:44][CH3:45])[N:40]=3)=[O:27])=[CH:24][N:25]=[C:19]2[CH:18]=1.C(=O)([O-])[O-].[K+].[K+].O.CN(C=O)C.CC#N>O.CO.C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:46]([C:31]1[C:30]2[C:34](=[CH:35][CH:36]=[CH:37][C:29]=2[NH:28][C:26]([C:23]2[N:20]3[CH:21]=[CH:22][C:17]([C:5]4[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=4)=[CH:18][C:19]3=[N:25][CH:24]=2)=[O:27])[N:33]([CH2:38][C:39]2[CH:43]=[CH:42][N:41]([CH2:44][CH3:45])[N:40]=2)[N:32]=1)[CH3:47]

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 672612817-bromo-N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideHCID 86672217water DMF CH3CN

生成物 1

HCID 67259773N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide収率 61.2%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
80 °C

実験手順

A dry, 10 mL round bottom flask equipped with a reflux condenser and a nitrogen line was charged with 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (25.4 mg, 0.122 mmol), 7-bromo-N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (50 mg, 0.102 mmol), Pd(PPh3)4 (5.9 mg, 0.005 mmol), and potassium carbonate (70 mg, 0.51 mmol). To the flask was added a water:DMF:CH3CN (1:1:4.5; 0.3:0.3:1.4 mL) mixture, and the reaction mixture was degassed under nitrogen, and heated at 80° C. for 5 hours. The cooled reaction mixture was diluted with water, the resulting suspension was extracted thoroughly with EtOAc and DCM, the combined organic extracts were dried over anhydrous sodium sulfate, and concentrated to afford the crude product. The crude product was subjected to preparative thin-layer chromatography on silica with 5% MeOH-DCM as eluent to afford 30.8 mg of product as a yellow solid. MS (ES+APCI) m/z=494 (M+H) detected

後処理

  1. customA dry, 10 mL round bottom flask equipped with a reflux condenser
  2. customthe reaction mixture was degassed under nitrogen
  3. customThe cooled reaction mixture
  4. extractionthe resulting suspension was extracted thoroughly with EtOAc and DCM
  5. dry with materialthe combined organic extracts were dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto afford the crude product

出典と根拠

ORDレコード
ord-40f9658ebc6e4982bbce6770cd2829e5
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

反応ノート

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