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

HRID 269587

반응식

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 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, 화합물촉매HCID 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
특허 번호
US07446222B2

연결된 노트

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