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

HRID 1521335노트

반응식

HRID 1521335 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
100 °C

실험 절차

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;

후처리

  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

출처 및 근거

ORD 기록
ord-7161f231263748d19d520849a0d5ce58
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073921B2

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