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Potassium Carbonate → Ethyl 5-{2'-[(phenylmethyl)oxy]-2-biphenylyl}-3-pyridinecarboxylate

HRID 269587
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HRID 269587 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:13]1([CH2:19][O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CCOCC.O.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>[C:13]1([CH2:19][O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:2]2[CH:12]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]=[N:4][CH:3]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 140785Ethyl 5-bromopyridine-3-carboxylateHCID 587309902'-Benzyloxy-biphenyl-2-boronic acid

생성물 1

HCID 58730994Ethyl 5-{2'-[(phenylmethyl)oxy]-2-biphenylyl}-3-pyridinecarboxylate수율 80.6%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물
촉매
HCID 21584184Diethylether water용매

반응 조건

온도
90 °C

실험 절차

A mixture of ethyl 5-bromonicotinate (46 mg, 0.2 mmol), {2′-[(phenylmethyl)oxy]-2-biphenylyl}boronic acid (61 mg, 0.2 mmol), potassium carbonate (221 mg, 1.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (23 mg, 0.02 mmol) was stirred and heated at 90° C. under nitrogen for 2 hours. After cooling the mixture was diluted with ether/water and the organic phase dried (magnesium sulphate), evaporated and chromatographed on silica eluting with ethyl acetate/iso-hexane (1:5) to give 66 mg of colourless gum.

후처리

  1. temperatureAfter cooling the mixture
  2. dry with materialthe organic phase dried (magnesium sulphate)
  3. customevaporated
  4. customchromatographed on silica eluting with ethyl acetate/iso-hexane (1:5)

출처 및 근거

ORD 기록
ord-42d232ef5de84170bcdcc8a7f6ebcff4
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07446222B2

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