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Sodium Carbonate → 5-(1-Methyl-1H-pyrazol-5-yl)-2-[(phenyl methyl)oxy]-N-3-pyridinylbenzamide

HRID 1623834
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HRID 1623834 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:8].[CH3:25][N:26]1[C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][CH:28]=[N:27]1.C(=O)([O-])[O-].[Na+].[Na+]>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.COCCOC>[CH3:25][N:26]1[C:30]([C:2]2[CH:3]=[CH:4][C:5]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:6]([CH:16]=2)[C:7]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:29][CH:28]=[N:27]1
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 49129081-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 369825032-(benzyloxy)-5-bromo-N-(pyridin-3-yl)benzamide

생성물 1

HCID 671070005-(1-Methyl-1H-pyrazol-5-yl)-2-[(phenyl methyl)oxy]-N-3-pyridinylbenzamide

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물
촉매
HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
120 °C

실험 절차

To a microwave vial was added 5-bromo-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in example 2; 100 mg, 0.26 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (59.7 mg, 0.29 mmol), 1,2-dimethoxyethane (2 ml), 1M sodium carbonate (0.52 ml, 0.52 mmol) and tetrakis(triphenylphosphine)palladium(0) (18.09 mg, 0.02 mmol). The vial was sealed and heated to 120° C. for 25 min under microwave conditions. The mixture was evaporated and water (5 ml) was added to the residue, the mixture was extracted with ethyl acetate (3×10 ml). The organics were combined and evaporated in vacuo and the residue was purified using the MDAP to yield the title compound. 22 mg.

후처리

  1. customThe vial was sealed
  2. customThe mixture was evaporated
  3. additionwater (5 ml) was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate (3×10 ml)
  5. customevaporated in vacuo
  6. customthe residue was purified

출처 및 근거

ORD 기록
ord-91da9eefefbb4ae28e9a1aa2ca4d3ea7
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08778939B2

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