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Sodium Carbonate → 2-[(Phenylmethyl)oxy]-5-(1H-pyrazol-4-yl)-N-3-pyridinylbenzamide

HRID 1623837
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HRID 1623837 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].CC1(C)C(C)(C)OB([C:33]2[CH:34]=[N:35][N:36](C(OC(C)(C)C)=O)[CH:37]=2)O1.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.O1CCOCC1>[C:19]1([CH2:18][O:17][C:5]2[CH:4]=[CH:3][C:2]([C:33]3[CH:34]=[N:35][NH:36][CH:37]=3)=[CH:16][C:6]=2[C:7]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:8])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 369825032-(benzyloxy)-5-bromo-N-(pyridin-3-yl)benzamide

생성물 1

HCID 671080462-[(Phenylmethyl)oxy]-5-(1H-pyrazol-4-yl)-N-3-pyridinylbenzamide

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 312751,4-Dioxane용매

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; 310 mg, 0.81 mmol), 1,1-dimethylethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (262 mg, 0.89 mmol), 1,4-dioxane (3 ml), sodium carbonate (1.62 ml, 1.62 mmol) and tetrakis(triphenylphosphine)palladium(0) (56.1 mg, 0.05 mmol). The vial was sealed and heated to 120° C. for 25 min under microwave conditions. The mixture was evaporated under reduced pressure 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 under reduced pressure, and the residue was purified using the MDAP to yield the title compound. 44 mg.

후처리

  1. customThe vial was sealed
  2. customThe mixture was evaporated under reduced pressure and water (5 ml)
  3. additionwas added to the residue
  4. extractionThe mixture was extracted with ethyl acetate (3×10 ml)
  5. customevaporated under reduced pressure
  6. customthe residue was purified

출처 및 근거

ORD 기록
ord-4a2b9882de1c4a57881199719b749b31
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08778939B2

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