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Sodium Carbonate → Benzyl 2-(benzyloxy)-5-(pyridin-4-yl)benzoate

HRID 1623699
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HRID 1623699 반응식
C([O-])([O-])=O.[Na+].[Na+].[N:7]1[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][CH:8]=1.[CH2:16]([O:23][C:24]1[CH:39]=[CH:38][C:37](Br)=[CH:36][C:25]=1[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCOCC1.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:17]1([CH2:16][O:23][C:24]2[CH:39]=[CH:38][C:37]([C:10]3[CH:11]=[CH:12][N:7]=[CH:8][CH:9]=3)=[CH:36][C:25]=2[C:26]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:27])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
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참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 17750009Benzyl 2-(benzyloxy)-5-bromobenzoate

생성물 1

HCID 66990917Benzyl 2-(benzyloxy)-5-(pyridin-4-yl)benzoate

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매
HCID 962
Water
용매
HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

Na2CO3 (0.53 g, 5.00 mmol), followed by pyridin-4-ylboronic acid (0.34 g, 2.75 mmol) and Pd(Ph3P)4 (0.144 g, 0.125 mmol) were added to a mixture of benzyl 2-(benzyloxy)-5-bromobenzoate (may be prepared as described in Description 4; 1.0 g, 2.50 mmol) in 1,4-dioxane (25 ml) and water (5 ml) under nitrogen. After addition, the mixture was stirred at 90° C. for 4 hours. The reaction mixture was evaporated to give brown crude product, which was purified by chromatography (silica gel, 40 g, eluent: ethyl acetate/petroleum ether=1:2, 1.2 L) to yield the title compound as a white solid. 0.81 g.

후처리

  1. additionAfter addition
  2. customThe reaction mixture was evaporated
  3. customto give brown crude product, which
  4. customwas purified by chromatography (silica gel, 40 g, eluent: ethyl acetate/petroleum ether=1:2, 1.2 L)

출처 및 근거

ORD 기록
ord-55c89b0d85cf4c90ace31f390dbfde79
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08778939B2

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