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Potassium Carbonate → 1h-Pyrazole-3-carboxamide,4-[3-(hydroxymethyl)phenyl]-1-[(4-methoxyphenyl)methyl]-n-phenyl-

HRID 659806
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HRID 659806 반응식
[C:1]1([NH:7][C:8]([C:10]2[C:14](I)=[CH:13][N:12]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[N:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[OH:31][CH2:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1>C(O)C.C1(C)C=CC=CC=1.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:1]1([NH:7][C:8]([C:10]2[C:14]([C:37]3[CH:36]=[CH:35][CH:34]=[C:33]([CH2:32][OH:31])[CH:38]=3)=[CH:13][N:12]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[N:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 668573141h-Pyrazole-3-carboxamide,4-iodo-1-[(4-methoxyphenyl)methyl]-n-phenyl-

생성물 1

HCID 668554221h-Pyrazole-3-carboxamide,4-[3-(hydroxymethyl)phenyl]-1-[(4-methoxyphenyl)methyl]-n-phenyl-수율 131.9%

시약·촉매·용매 2

HCID 178418851
HCID 178418851, 화합물
촉매
HCID 86587398Ethanol toluene water용매

반응 조건

온도
120 °C

실험 절차

A mixture of 4-iodo-1-(4-methoxy-benzyl)-1H-pyrazole-3-carboxylic acid phenylamide (50 mg; 0.11 mmol), bis(tri-tert-butylphosphine)palladium (12 mg), potassium carbonate (100 mg; 0.66 mmol) and 3-(hydroxymethyl)benzene boronic acid (21 mg; 0.14 mmol) in ethanol/toluene/water (4 ml:1 ml:1 ml) was heated at 120° C. (50 W) for 15 minutes in a CEM Discover microwave synthesiser. The reaction was evaporated and the residue partitioned between ethyl acetate and brine. The ethyl acetate layer was separated, dried (MgSO4), filtered and evaporated and the crude material purified by flash column chromatography eluting with 1:2 then 2:1 ethyl acetate/hexane. Product containing fractions were combined and evaporated to give 60 mg of 4-(3-hydroxymethyl-phenyl)-1-(4-methoxy-benzyl)-1H-pyrazole-3-carboxylic acid phenylamide.

후처리

  1. customThe reaction was evaporated
  2. customthe residue partitioned between ethyl acetate and brine
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customthe crude material purified by flash column chromatography
  8. washeluting with 1:2
  9. additionProduct containing fractions
  10. customevaporated

출처 및 근거

ORD 기록
ord-95199559413043e8ace40c8cf8fe75c1
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08080666B2

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