Potassium Carbonate → Methyl 4-amino-2'-bromo-2-biphenylcarboxylate

HRID 269564

반응식

HRID 269564 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.[NH2:11][C:12]1[CH:13]=[CH:14][C:15](Br)=[C:16]([CH:21]=1)[C:17]([O:19][CH3:20])=[O:18].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1.C(O)C>C(OCC)C.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>[NH2:11][C:12]1[CH:21]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[C:15]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])=[CH:14][CH:13]=1

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 245495Methyl 5-amino-2-bromobenzoateHCID 2773294(2-Bromophenyl)boronic acidHCID 21863594Toluene ethanol

생성물 1

HCID 58730987Methyl 4-amino-2'-bromo-2-biphenylcarboxylate

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 3283Diethyl Ether용매

반응 조건

온도
90 °C

실험 절차

A mixture of 2-bromophenyl boronic acid (600 mg, 3.0 mmol), methyl 5-amino-2-bromobenzoate (1.5 g, 6.5 mmol), potassium carbonate (2.07 g, 15 mmol) and tetrakis(triphenylphosphine)palladium (0) (345 mg, 5 mol %) in 1:1 toluene/ethanol (20 ml) was stirred and heated at 90° C. under nitrogen for 12 hours. After cooling the mixture was diluted with diethyl ether and water and the organic phase dried (MgSO4) and evaporated to dryness. The residue was chromatographed with dichloromethane/iso-hexane (1:2->1:1) to yield the title compound as a pale yellow gum. (682 mg, 74%).

후처리

  1. temperatureAfter cooling the mixture
  2. dry with materialthe organic phase dried (MgSO4)
  3. customevaporated to dryness
  4. customThe residue was chromatographed with dichloromethane/iso-hexane (1:2->1:1)

출처 및 근거

ORD 기록
ord-273f753770b94019aec781ec869b4b74
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446222B2

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